Chloroform → HCID 130126346, compound

HRID 536778Notes

Reaction equation

HRID 536778 reaction equation
C=C[C@H](O)C#[C:5][C:6]#[C:7][CH2:8][C@H:9](O)[C@@H:10]([OH:18])[CH2:11][CH2:12]CCCCC.C(Cl)(Cl)Cl>O>[CH2:12]=[CH:11][CH:10]([OH:18])[C:9]#[C:8][C:7]#[C:6][CH3:5]

Participants

4

Reactant 2

HCID 6212ChloroformHCID 46184189HCID 46184189, compound

Product 1

HCID 130126346HCID 130126346, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(S)-8-(4S,5S)-5-heptyl-2,2-dimethyl-1,3-dioxolan-4-yl)octa-1-en-4,6-diyn-3-ol, ent-panaxytriol acetonide was prepared from (3S,9S,10S)-heptadeca-1-en-4,6-diyne-3,9,10-triol, ent-panaxytriol, by the method described in Yun, H.; Chou, T. C.; Dong, H.; Tian, Y.; Li, Y-M.; Danishefsky, S. J. J. Org Chem. 2005, 70, 10375, yielding the product with: [α]19.3D-70.5 (c=0.13, CHCl3). 1H NMR (300 MHz, CDCl3) δ 5.94 (ddd, 17.1 Hz, 10.2 Hz, 5.4 Hz, 1H), 5.47 (d, 17.1, 1H), 5.26 (d, 10.2 Hz, 1H), 4.92 (d, 5.1 Hz, 1H), 4.36 (t, 6 Hz, 1H), 3.77 (m, 2H), 2.60 (m, 2H), 1.7-1.2 (m, 12H), 1.40 (s, 6H), 0.88 (t, 6.9 Hz, 3H). LRMS (APCI+) found 319.0, [M]+, 333.04, [M+H2O]+.

Sources & evidence

ORD record
ord-911b7286c17147909c967582309245e6
Source dataset
uspto-grants-2014_10
Patent number
US08859615B2

Reaction notes

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