(2R,3R)-Dibenzyl 2,3-dihydroxysuccinate

Base Information

• Chemical Name: (2R,3R)-Dibenzyl 2,3-dihydroxysuccinate
• CAS No.: 622-00-4
• Molecular Formula: C18H18 O6
• Molecular Weight: 330.337
• Hs Code.: 2918130000
• DSSTox Substance ID: DTXSID60427315
• Nikkaji Number: J95.566C
• Wikidata: Q72463700
• Mol file: 622-00-4.mol

Synonyms:622-00-4;L-Tartaric Acid Dibenzyl Ester;(2R,3R)-Dibenzyl 2,3-dihydroxysuccinate;Dibenzyl L-Tartrate;dibenzyl (2R,3R)-2,3-dihydroxybutanedioate;rel-(2R,3R)-Dibenzyl 2,3-dihydroxysuccinate;4079-56-5;L-(+)-Dibenzyl Tartrate;SCHEMBL366832;DTXSID60427315;LCKIPSGLXMCAOF-HZPDHXFCSA-N;AMY41887;MFCD00674554;AKOS000277853;CS-W014506;T1671;W12796;A852373;(+)-Dibenzyl L-tartrate, for chiral derivatization, >=98.0%

Chemical Property of (2R,3R)-Dibenzyl 2,3-dihydroxysuccinate

Chemical Property:

• Vapor Pressure: 4.64E-10mmHg at 25°C
• Melting Point: 51-54 °C
• Refractive Index: -13 ° (C=1, Acetone)
• Boiling Point: 480.9°C at 760 mmHg
• PKA: 11.38±0.20(Predicted)
• Flash Point: 171.5°C
• PSA: 93.06000
• Density: 1.312g/cm³
• LogP: 1.19500
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 330.11033829
• Heavy Atom Count: 24
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

(2R,3R)-Dibenzyl2,3-dihydroxysuccinate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)C(C(C(=O)OCC2=CC=CC=C2)O)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)[C@@H]([C@H](C(=O)OCC2=CC=CC=C2)O)O

Technology Process of (2R,3R)-Dibenzyl 2,3-dihydroxysuccinate

There total 8 articles about (2R,3R)-Dibenzyl 2,3-dihydroxysuccinate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

L-Tartaric acid (87-69-4,138508-61-9) + benzyl alcohol (100-51-6,185532-71-2) → dibenzyl (2R,3R)-2,3-dihydroxybutanedioate (622-00-4)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 24h; Reflux;

DOI:10.1039/c7cc03320f

Reference yield: 40.0%

benzylglyoxylate (52709-42-9) → benzyl glycolate (30379-58-9) + dibenzyl (+)-tartrate (622-00-4,4079-56-5,4079-57-6,4136-22-5,93993-87-4)

Guidance literature:

With 1,2-dimethoxyethane; zinc copper; titanium tetrachloride; In dichloromethane; at -23 ℃;

Reference yield:

dibenzyl (4R,5R)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide (643028-20-0) → dibenzyl (2R,3R)-2,3-dihydroxybutanedioate (622-00-4) + (2S,3R)-Dibenzyl 2-Azido-3-hydroxysuccinate (128971-83-5)

Guidance literature:

dibenzyl (4R,5R)-1,3,2-dioxathiolane-4,5-dicarboxylate 2-oxide; With sodium azide; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

With water; In dichloromethane; for 2h;

DOI:10.1016/j.tetasy.2003.09.015

upstream raw materials:

L-Tartaric acid

benzyl alcohol

benzylglyoxylate

benzyl bromide

Downstream raw materials:

(4R,5R)-bis(benzyloxycarbonyl)-2-chloro-1,3,2-dioxaphospholane

(R,R)-dibenzyl tartrate mono-3,5-di(tert-butyl)benzoate

(2S)-benzyl 6-{[(benzyloxy)-2-oxoethyl]amino}-2-{[(benzyloxy)carbonyl]amino}hexanoate

dibenzyl 2,3-bis(dibenzylphospho)-L-tartrate

Refernces

• 1、 Moitra, Parikshit,Kumar, Krishan,Sarkar, Sourav,Kondaiah, Paturu,Duan, Wei,Bhattacharya, Santanu. "New pH-responsive gemini lipid derived co-liposomes for efficacious doxorubicin delivery to drug resistant cancer cells". supporting information. p. 8184 - 8187. Retrieved 2017/07/24.
• 2、 Zhang, Yi,Dai, Yuchi,Li, Guigen,Cheng, Xu. "The catalytic synthesis of carboniolamide: The role of sp 3 hybridized oxygen". supporting information. p. 2644 - 2648. Retrieved 2015/02/02.