(3S,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-5-(4-methoxy-benzylsulfanyl)-pentanoic acid allyl ester

Base Information

Chemical Name:(3S,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-5-(4-methoxy-benzylsulfanyl)-pentanoic acid allyl ester
CAS No.:877814-35-2
Molecular Formula:C₂₁H₃₁NO₆S
Molecular Weight:425.546
Hs Code.:

Synonyms:(3S,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-5-(4-methoxy-benzylsulfanyl)-pentanoic acid allyl ester

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Chemical Property of (3S,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-5-(4-methoxy-benzylsulfanyl)-pentanoic acid allyl ester

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Technology Process of (3S,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-5-(4-methoxy-benzylsulfanyl)-pentanoic acid allyl ester

There total 3 articles about (3S,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-5-(4-methoxy-benzylsulfanyl)-pentanoic acid allyl 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:

: 116430-17-2
[1-formyl-2-(4-methoxy-benzylsulfanyl)-ethyl]-carbamic acid tert-butyl ester

: 40630-84-0
allyl bromoacetate

: 877814-35-2
(3S,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-5-(4-methoxy-benzylsulfanyl)-pentanoic acid allyl ester

Guidance literature:: With zinc; In tetrahydrofuran; at 20 - 60 ℃; for 0.5h;
DOI:10.1021/ol052755m

Reference yield:

: 877814-34-1
[2-(4-methoxy-benzylsulfanyl)-1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester

: 877814-35-2
(3S,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-5-(4-methoxy-benzylsulfanyl)-pentanoic acid allyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: DIBALH / tetrahydrofuran; toluene / 0.5 h / -78 °C

2: 1.9 g / Zn / tetrahydrofuran / 0.5 h / 20 - 60 °C

With diisobutylaluminium hydride; zinc; In tetrahydrofuran; toluene; 2: Reformatsky reaction;
DOI:10.1021/ol052755m

Reference yield:

: 18942-46-6,58290-35-0
N-(tert-butyloxycarbonyl)-S-(4-methoxybenzyl)cysteine

: 877814-35-2
(3S,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-5-(4-methoxy-benzylsulfanyl)-pentanoic acid allyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / HOBt*H₂O; Et₃N; EDC*HCl / dimethylformamide / 10 h / 20 °C

2: DIBALH / tetrahydrofuran; toluene / 0.5 h / -78 °C

3: 1.9 g / Zn / tetrahydrofuran / 0.5 h / 20 - 60 °C

With diisobutylaluminium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; zinc; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 1: Weinreb amidation / 3: Reformatsky reaction;
DOI:10.1021/ol052755m