methyl (2S,4R)-1-((((2S,3R)-3-(((benzyloxy)carbonyl)amino)-4-methoxy-4-oxobutan-2-yl)thio)carbonothioyl)-4-hydroxypyrrolidine-2-carboxylate

Base Information

Chemical Name:methyl (2S,4R)-1-((((2S,3R)-3-(((benzyloxy)carbonyl)amino)-4-methoxy-4-oxobutan-2-yl)thio)carbonothioyl)-4-hydroxypyrrolidine-2-carboxylate
CAS No.:1394239-80-5
Molecular Formula:C₂₀H₂₆N₂O₇S₂
Molecular Weight:470.568
Hs Code.:

Synonyms:methyl (2S,4R)-1-((((2S,3R)-3-(((benzyloxy)carbonyl)amino)-4-methoxy-4-oxobutan-2-yl)thio)carbonothioyl)-4-hydroxypyrrolidine-2-carboxylate

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Chemical Property of methyl (2S,4R)-1-((((2S,3R)-3-(((benzyloxy)carbonyl)amino)-4-methoxy-4-oxobutan-2-yl)thio)carbonothioyl)-4-hydroxypyrrolidine-2-carboxylate

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Technology Process of methyl (2S,4R)-1-((((2S,3R)-3-(((benzyloxy)carbonyl)amino)-4-methoxy-4-oxobutan-2-yl)thio)carbonothioyl)-4-hydroxypyrrolidine-2-carboxylate

There total 2 articles about methyl (2S,4R)-1-((((2S,3R)-3-(((benzyloxy)carbonyl)amino)-4-methoxy-4-oxobutan-2-yl)thio)carbonothioyl)-4-hydroxypyrrolidine-2-carboxylate 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: 85.0%

: 75-15-0,12122-00-8
carbon disulfide

: 1224632-39-6
(4S,5R)-3-benzyl 4-methyl 5-methyl-1,2,3-oxathiazolidine-3,4-dicarboxylate 2,2-dioxide

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 1394239-80-5
methyl (2S,4R)-1-((((2S,3R)-3-(((benzyloxy)carbonyl)amino)-4-methoxy-4-oxobutan-2-yl)thio)carbonothioyl)-4-hydroxypyrrolidine-2-carboxylate

Guidance literature:: carbon disulfide; L-4-hydroxyproline methyl ester hydrochloride; In N,N-dimethyl-formamide; at 0 - 5 ℃;

(4S,5R)-3-benzyl 4-methyl 5-methyl-1,2,3-oxathiazolidine-3,4-dicarboxylate 2,2-dioxide; In N,N-dimethyl-formamide; at 20 ℃; for 12h; stereoselective reaction;
DOI:10.1039/c2cc32894a

Reference yield:

: 57224-63-2
methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate

: 1394239-80-5
methyl (2S,4R)-1-((((2S,3R)-3-(((benzyloxy)carbonyl)amino)-4-methoxy-4-oxobutan-2-yl)thio)carbonothioyl)-4-hydroxypyrrolidine-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: thionyl chloride; pyridine / acetonitrile / -40 - 20 °C / Inert atmosphere

1.2: Cooling with ice

2.1: N,N-dimethyl-formamide / 0 - 5 °C

2.2: 12 h / 20 °C

With pyridine; thionyl chloride; In N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/c2cc32894a