Butanedioic acid, 2-bromo-3-hydroxy-, dimethyl ester, (2R,3S)-rel- (9CI)

Base Information

• Chemical Name: Butanedioic acid, 2-bromo-3-hydroxy-, dimethyl ester, (2R,3S)-rel- (9CI)
• CAS No.: 256530-26-4
• Molecular Formula: C₆H₉BrO₅
• Molecular Weight: 241.038
• Mol file: 256530-26-4.mol

Synonyms:Butanedioicacid, 2-bromo-3-hydroxy-, dimethyl ester, (2R,3S)-rel- (9CI)

Chemical Property of Butanedioic acid, 2-bromo-3-hydroxy-, dimethyl ester, (2R,3S)-rel- (9CI)

Chemical Property:

• PSA: 72.83000
• LogP: -0.54320

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Butanedioic acid, 2-bromo-3-hydroxy-, dimethyl ester, (2R,3S)-rel- (9CI)

There total 6 articles about Butanedioic acid, 2-bromo-3-hydroxy-, dimethyl ester, (2R,3S)-rel- (9CI) 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: 82.0%

dimethyl (2R)-acetoxy-(3S)-bromosuccinate (78816-00-9) → dimethyl (2S,3R)-2-bromo-3-hydroxysuccinate (109874-90-0,256530-26-4)

Guidance literature:

With hydrogenchloride; In methanol; at 22 ℃; for 46h;

DOI:10.1021/ja00350a059

Reference yield: 75.0%

Dimethyl D-tartrate (13171-64-7) → dimethyl (2R,3R)-2-bromo-3-hydroxysuccinate (749917-66-6,256530-26-4)

Guidance literature:

With hydrogen bromide; In acetic acid;

Reference yield:

dimethyl L-tartrate (608-68-4) → dimethyl (2S,3R)-2-bromo-3-hydroxysuccinate (109874-90-0,256530-26-4)

Guidance literature:

With methanol; hydrogen bromide; acetic acid; acetyl chloride; Yield given. Multistep reaction; 1) r.t., 10 h, 2) reflux, 6 h;

DOI:10.1016/S0040-4020(01)92187-8

upstream raw materials:

dimethyl L-tartrate

dimethyl (2R)-acetoxy-(3S)-bromosuccinate

dimethyl (R,R)-O-acetyl-tartrate

(4R,5R)-2,2-Dioxo-2λ⁶-[1,3,2]dioxathiolane-4,5-dicarboxylic acid dimethyl ester

Downstream raw materials:

2-amino-3-hydroxy-succinic acid dimethyl ester

(3-hydroxymethyl-oxiranyl)-methanol

Refernces

• 1、 France, Boyaud,Bruno, Viguier,Nicolas, Inguimbert. "Synthesis of a protected derivative of (2R,3R)-β-hydroxyaspartic acid suitable for Fmoc-based solid phase synthesis". . p. 158 - 161. Retrieved 2013/02/22.
• 2、 -. "Process for the production of pentostatin aglycone and pentostatin". Page 7. . Retrieved 2010/02/08.