Trithiocarbonic acid (2R,3S)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl ester 2-(4-nitro-benzyloxycarbonylamino)-ethyl ester

Base Information

• Chemical Name: Trithiocarbonic acid (2R,3S)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl ester 2-(4-nitro-benzyloxycarbonylamino)-ethyl ester
• CAS No.: 76855-70-4
• Molecular Formula: C₂₂H₃₃N₃O₆S₃Si
• Molecular Weight: 559.804

Synonyms:

Chemical Property of Trithiocarbonic acid (2R,3S)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl ester 2-(4-nitro-benzyloxycarbonylamino)-ethyl ester

Chemical Property:

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Technology Process of Trithiocarbonic acid (2R,3S)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl ester 2-(4-nitro-benzyloxycarbonylamino)-ethyl ester

There total 4 articles about Trithiocarbonic acid (2R,3S)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl ester 2-(4-nitro-benzyloxycarbonylamino)-ethyl 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:

2-(4-nitrobenzyloxycarbonylamino)ethanethiol (65750-59-6) → Trithiocarbonic acid (2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl ester 2-(4-nitro-benzyloxycarbonylamino)-ethyl ester (76855-70-4,81076-29-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methoxide / methanol / 20 h / 0 °C

2: methanol / 0.67 h / -10 °C

With sodium methylate; In methanol;

DOI:10.1248/cpb.29.3158

Reference yield:

2-(4-nitrobenzyloxycarbonylamino)ethanethiol (65750-59-6) → Trithiocarbonic acid (2R,3S)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl ester 2-(4-nitro-benzyloxycarbonylamino)-ethyl ester (76855-70-4,81076-29-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methoxide / methanol / 20 h / 0 °C

2: methanol / 0.67 h / -10 °C

With sodium methylate; In methanol;

DOI:10.1248/cpb.29.3158

Reference yield:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) + C11H11N2O4S3(1-)*Na(1+) (78902-89-3) → Trithiocarbonic acid (2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl ester 2-(4-nitro-benzyloxycarbonylamino)-ethyl ester (76855-70-4,81076-29-1)

Guidance literature:

In methanol; at -10 ℃; for 0.666667h; Yield given;

DOI:10.1248/cpb.29.3158

upstream raw materials:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

C₁₁H₁₁N₂O₄S₃^(1-)*Na⁽¹⁺⁾

2-(4-nitrobenzyloxycarbonylamino)ethanethiol

(3R,4R)-4-acetoxy-3-<(S)-1-(tert-butyldimethylsilyloxy)ethyl>-2-azetidinone

Downstream raw materials:

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanylthiocarbonylsulfanyl]-4-oxo-azetidin-1-yl}-hydroxy-acetic acid 4-nitro-benzyl ester

{(2R,3S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanylthiocarbonylsulfanyl]-4-oxo-azetidin-1-yl}-hydroxy-acetic acid 4-nitro-benzyl ester

{(2R,3S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanylthiocarbonylsulfanyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester

(5R,6S)-6-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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