S-triphenylmethyl N-(carbobenzyloxy)-O-(tert-butyldimethylsilyl)-L-threoninethiohydroxamate

Base Information

• Chemical Name: S-triphenylmethyl N-(carbobenzyloxy)-O-(tert-butyldimethylsilyl)-L-threoninethiohydroxamate
• CAS No.: 102652-68-6
• Molecular Formula: C₃₇H₄₄N₂O₄SSi
• Molecular Weight: 640.919
• Mol file: 102652-68-6.mol

Synonyms:S-triphenylmethyl N-(carbobenzyloxy)-O-(tert-butyldimethylsilyl)-L-threoninethiohydroxamate

Chemical Property of S-triphenylmethyl N-(carbobenzyloxy)-O-(tert-butyldimethylsilyl)-L-threoninethiohydroxamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of S-triphenylmethyl N-(carbobenzyloxy)-O-(tert-butyldimethylsilyl)-L-threoninethiohydroxamate

There total 5 articles about S-triphenylmethyl N-(carbobenzyloxy)-O-(tert-butyldimethylsilyl)-L-threoninethiohydroxamate 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: 63.0%

Triphenylmethanesulfenamide (38499-08-0) + (2S,3R)-2-(benzyloxycarbonylamino)-3-tertiary-butyldimethylsilyloxybutanoic acid (94820-26-5) → S-triphenylmethyl N-(carbobenzyloxy)-O-(tert-butyldimethylsilyl)-L-threoninethiohydroxamate (102652-68-6)

Guidance literature:

With pyridine; oxalyl dichloride; N,N-dimethyl-formamide; In acetonitrile; for 1h; Ambient temperature;

DOI:10.1021/jo00366a010

Reference yield:

triphenylmethanethiol (3695-77-0) → S-triphenylmethyl N-(carbobenzyloxy)-O-(tert-butyldimethylsilyl)-L-threoninethiohydroxamate (102652-68-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / SO₂Cl₂ / diethyl ether; benzene / 0.5 h

2: 55 percent / NH₃ / diethyl ether

3: 63 percent / DMF, oxalyl chloride, pyridine / acetonitrile / 1 h / Ambient temperature

With pyridine; sulfuryl dichloride; oxalyl dichloride; ammonia; N,N-dimethyl-formamide; In diethyl ether; acetonitrile; benzene;

DOI:10.1021/jo00366a010

Reference yield:

tritylsulfenyl chloride (24165-03-5) → S-triphenylmethyl N-(carbobenzyloxy)-O-(tert-butyldimethylsilyl)-L-threoninethiohydroxamate (102652-68-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / NH₃ / diethyl ether

2: 63 percent / DMF, oxalyl chloride, pyridine / acetonitrile / 1 h / Ambient temperature

With pyridine; oxalyl dichloride; ammonia; N,N-dimethyl-formamide; In diethyl ether; acetonitrile;

DOI:10.1021/jo00366a010

upstream raw materials:

Triphenylmethanesulfenamide

(2S,3R)-2-(benzyloxycarbonylamino)-3-tertiary-butyldimethylsilyloxybutanoic acid

triphenylmethanethiol

tritylsulfenyl chloride

Downstream raw materials:

S-triphenylmethyl N-(carbobenzyloxy)-L-threoninethiohydroxamate