(3R,4R)-4-アセトキシ-3-[(R)-(tert-ブチルジメチルシリルオキシ)エチル]-2-アゼチジノン

(3R,4R)-4-Acetoxy-3-((R)-(tert-butyldimethylsilyloxy)ethyl)-2-azetidinone

HCID 13073890CAS 76855-69-1

部分構造検索類似構造を探す

基本情報

標準SMILES: CC(=O)O[C@H]1NC(=O)[C@H]1[C@@H](C)O[Si](C)(C)C(C)(C)C
InChIKey: GWHDKFODLYVMQG-HLUHBDAQSA-N
分子式: C13H25NO4Si
平均分子量: 287.43 g/mol
単同位体質量: 287.15528481

名称と識別子

優先名称: (3R,4R)-4-Acetoxy-3-((R)-(tert-butyldimethylsilyloxy)ethyl)-2-azetidinone
IUPAC: [(2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate
現地名: (3R,4R)-4-アセトキシ-3-[(R)-(tert-ブチルジメチルシリルオキシ)エチル]-2-アゼチジノン
英語名: (3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
分子式: C13H25NO4Si
分子量: 287.43

名称と別名

RefChem:401044(3R,4R)-4-Acetoxy-3-((R)-(tert-butyldimethylsilyloxy)ethyl)-2-azetidinone(3R,4R)-4-Acetoxy-3-[(R)-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone623-445-8(3s,4r)-4-acetoxy-3-[(r)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one85954-95-6(2R,3S)-3-((R)-1-((tert-Butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl acetateC13H25NO4SiSCHEMBL1143665(2R,3S)-3-((R)-1-((tert-Butyldimethylsilyl)-oxy)ethyl)-4-oxoazetidin-2-yl acetateAKOS015901618(2R,3S)-3-((R)-1-((tert-Butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-ylacetate

名称をさらに表示

(3R,4R)-4-アセトキシ-3-[(R)-(tert-ブチルジメチルシリルオキシ)エチル]-2-アゼチジノン3-［1-（tert-ブチルジメチルシロキシ）エチル］-4-オキソ-2-アゼチジニル＝アセタート(3R,4R)-(+)-4-アセトキシ-3-[(R)-(T-ブチルジメチルシリルオキシ)エチル]-2-アゼチジノン(3R,4R)-4-アセトキシ-3-[(R)-1-(TERT-ブチルジメチルシリルオキシ)エチル]-2-アゼチジノン(2R,3R)-3-[(1R)-1-[(tert-ブチルジメチルシリル)オキシ]エチル]-4-オキソアゼチジン-2-イルアセタート(3R)-3α-[(1R)-1-(tert-ブチルジメチルシロキシ)エチル]-4β-アセトキシアゼチジン-2-オンアゼチドンアセトキシアゼチジノン4-AA4-ACETOXYAZETIDIN-2-ONEAzetidon(3R,4R)-4-ACETOXY-3-[(R)-(T-BUTYLDIMETHYLSILYLOXY)ETHYL]-2-AZETIDINONE(3R,4R)-4-ACETOXY-3-[(R)-1-(TERT-BUTYLDIMETHYLSILYLOXY)ETHYL]AZETIDIN-2-ONE(2R,3R)-3-((R)-1-(tert-butyldimethylsiloxy)ethyl)-4-oxoazetidin-2-yl acetate4-AOSA(3R<4AA(AOSA)AOSA (4-AA)

(3S, 4R)-4-acetoxy-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]-azetidin-2-one(3S,4R)-4-acetoxy-3-[(1R)-1-tert-butyldimethylsilyloxyethyl]azetidin-2-one(3S,4R)-4-acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone[(2R,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxo-azetidin-2-yl] acetate

データベース識別子

CAS: 76855-69-1
PubChem CID: 13073890
EC Number: 623-445-8
Nikkaji: J711.862G

物性

構造計算による物性

極性表面積: 64.6 Å²
水素結合供与体数: 1
水素結合受容体数: 4
回転可能結合数: 6
重原子数: 19
形式電荷: 0
複雑度: 375

物理化学的性質

融点: 107 · 107-109 °C(lit.)
比旋光度: 51 · 51 º (c=1, chloroform)
沸点: 358.3 · 358.3±27.0 °C(Predicted)
比重(密度): 1.03 · 1.03±0.1 g/cm3(Predicted)
貯蔵温度: 2 · 2-8°C
溶解性: almost transparency in Methanol
外見: powder to crystal
酸解離定数(Pka): 12.86 · 12.86±0.60(Predicted)
色: White to Almost white
InChI: InChI=1S/C13H25NO4Si/c1-8(18-19(6,7)13(3,4)5)10-11(16)14-12(10)17-9(2)15/h8,10,12H,1-7H3,(H,14,16)/t8-,10+,12-/m1/s1
InChIKey: GWHDKFODLYVMQG-UBHAPETDSA-N
SMILES: N1[C@H](OC(C)=O)[C@@H]([C@H](O[Si](C(C)(C)C)(C)C)C)C1=O
CAS データベース: 76855 · 76855-69-1(CAS DataBase Reference)

化学的性質

化学的特性white to light yellow crystal powde

安全と法規制

GHS分類

GHS Classification · 5 件

Warning

H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P261, P264+P265, P272, P273, P280, P302+P352, P305+P351+P338, P321, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Hazard Classes and CategoriesSkin Sens. 1 (100%)；Eye Irrit. 2 (100%)；Aquatic Chronic 2 (100%)

安全データ

wgk: 2
ridadr: UN 3077 9/PG 3
hs_code: 29337900
risk_code: 36-43-51/53
化審法: (5)-6118
hazard_code: Xi,N
safety_code: 24-26-37-61
hazard_class: 9
packing_group: III
Hazard Classifications: Aquatic Chronic 2Eye Irrit. 2Skin Sens. 1
ストレージクラス: 11 - Combustible Solids

化学と産業

応用分野

用途カルバベネムなどのβ-ラクタム抗生物質の合成原料。

使用(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one is an acetoxyazetidinone derivative used as an intermediate in the preparation of carbapenem antibiotics.

調製方法

純化方法Purify it by chromatography on silica gel (3 x 14cm) for 50g of ester using 20% EtOAc in n-hexane. The eluate is evaporated, and the residue is recrystallised from hexane (white fluffy crystals). [Leanza et al. Tetrahedron 39 2505 1983.]

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