(R)-2-((S)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-thiazolidine-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (R)-2-((S)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-thiazolidine-4-carboxylic acid methyl ester
• CAS No.: 252897-70-4
• Molecular Formula: C₃₁H₃₆N₂O₅S
• Molecular Weight: 548.703
• Mol file: 252897-70-4.mol

Synonyms:(R)-2-((S)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-thiazolidine-4-carboxylic acid methyl ester

Chemical Property of (R)-2-((S)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-thiazolidine-4-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-((S)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-thiazolidine-4-carboxylic acid methyl ester

There total 4 articles about (R)-2-((S)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-thiazolidine-4-carboxylic acid methyl ester 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: 95.0%

L-Cysteine methyl ester (2485-62-3) + Nα-Boc-O-trityl-L-serinal (252897-69-1) → (R)-2-((S)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-thiazolidine-4-carboxylic acid methyl ester (252897-70-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; benzene;

DOI:10.1016/S0040-4039(99)01654-8

Reference yield:

(1-hydroxymethyl-2-trityloxy-ethyl)-carbamic acid tert-butyl ester → (R)-2-((S)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-thiazolidine-4-carboxylic acid methyl ester (252897-70-4)

Guidance literature:

Multi-step reaction with 2 steps

1: KHSO₄ / H₂O

2: 95 percent / DIEA / CH₂Cl₂; benzene

With potassium hydrogensulfate; N-ethyl-N,N-diisopropylamine; In dichloromethane; water; benzene; 1: Oxidation / 2: Condensation;

DOI:10.1016/S0040-4039(99)01654-8

Reference yield:

Boc-Ser(Trt)-OH (252897-67-9) → (R)-2-((S)-1-tert-Butoxycarbonylamino-2-trityloxy-ethyl)-thiazolidine-4-carboxylic acid methyl ester (252897-70-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / BOP; DIEA / CH₂Cl₂ / 0.33 h

2: LAH / diethyl ether / 0.5 h / 0 °C

3: KHSO₄ / H₂O

4: 95 percent / DIEA / CH₂Cl₂; benzene

With potassium hydrogensulfate; lithium aluminium tetrahydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; water; benzene; 1: Condensation / 2: Reduction / 3: Oxidation / 4: Condensation;

DOI:10.1016/S0040-4039(99)01654-8

upstream raw materials:

L-Cysteine methyl ester

Nα-Boc-O-trityl-L-serinal

Boc-Ser(Trt)-OH

Boc-Ser(Trt)-N-methoxy-N-methyl amide

Downstream raw materials:

2-(1-tert-butoxycarbonylamino-2-trityloxy-ethyl)-thiazole-4-carboxylic acid methyl ester

2-((S)-1-Amino-2-trityloxy-ethyl)-thiazole-4-carboxylic acid methyl ester