(2S,3S)-Dibenzyl 2,3-dihydroxysuccinate
Basic information
- CAS
4136-22-5- Standard SMILES
O=C(OCc1ccccc1)[C@@H](O)[C@H](O)C(=O)OCc1ccccc1- InChIKey
LCKIPSGLXMCAOF-HOTGVXAUSA-N- Molecular formula
- C18H18O6
- Average molar mass
- 330.3 g/mol
- Monoisotopic mass
- 330.11033829
Names & identifiers
- Preferred name
- (2S,3S)-Dibenzyl 2,3-dihydroxysuccinate
- IUPAC
- dibenzyl (2S,3S)-2,3-dihydroxybutanedioate
- English name
- (-)-Dibenzyl D-tartrate
- Molecular formula
- C18H18O6
- Molecular weight
- 330.33
Names & synonyms
4136-22-5(2S,3S)-Dibenzyl 2,3-dihydroxysuccinate(-)-DIBENZYL D-TARTRATEdibenzyl (2S,3S)-2,3-dihydroxybutanedioateMFCD01863133(a")-Dibenzyl-D-tartrateDibenzyl (2S,3S)-2,3-DihydroxysuccinateD-(-)-Dibenzyl TartrateDibenzyl D-tartrate(2S,3S)-Dibenzyl2,3-dihydroxysuccinateD-DBTSCHEMBL6575848
Show more names
(-) Di Benzyl D Tartrate(?)-Dibenzyl D-tartrate2,3-dihydroxybutanedioic acid bis(phenylmethyl) esterDi Benzyl-D-Tartarate≥98.0% (sum of enantiomers, HPLC)(-)-Dibenzyl D-tartrate >=98.0% (sum of enantiomers, HPLC)
DTXSID30426597AKOS016842769CS-W011963AS-20132SY123842ST50320104W12797F213449
Database identifiers
- CAS
4136-22-5- PubChem CID
- 7010050
- DTXSID
DTXSID30426597- Nikkaji
- J1.801.127A
Properties
Computed structural properties
- XLogP
- 1.8
- Topological polar surface area
- 93.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 9
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 360
Physicochemical properties
- Melting point
- 65 · 65-68 °C
- Boiling point
- 480.9 · 480.9±25.0 °C(Predicted)
- Density
- 1.312 · 1.312±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- pka
- 11.38 · 11.38±0.20(Predicted)
- form
- powder
- optical activity
- 20 · [α]20/D 12.5±1°, c = 1.1% in acetone
- BRN
- 4787873 · 4787873
- InChI
- 1S/C18H18O6/c19-15(17(21)23-11-13-7-3-1-4-8-13)16(20)18(22)24-12-14-9-5-2-6-10-14/h1-10,15-16,19-20H,11-12H2/t15-,16-/m0/s1
- InChIKey
- LCKIPSGLXMCAOF-HOTGVXAUSA-N
- SMILES
- O[C@@H]([C@H](O)C(=O)OCc1ccccc1)C(=O)OCc2ccccc2
- UNSPSC Code
- 12352108 · 12352108
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 3-9
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
Uses(-)-Dibenzyl D-tartrate can be employed as a reactant to synthesize: 2,3-bis(8-Methoxyoctanoyl) dibenzyl tartrate (DBT) by reacting with 8-methoxyoctanoic acid in the presence of 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide (EDCI) as a coupling reagent. (-)-Chicoric acid (2,3-bis{[3-(3,4-dihydroxyphenyl)-1-oxoprop-2-enyl]oxy}butanedioic acid), as a potent inhibitor. Diesters of aziridine-2,3-dicarboxylic acid derivatives.
Upstream & downstream products
Downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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