(5R,6S)-6-(1,2-Dihydroxy-1-methyl-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

Base Information

Chemical Name:(5R,6S)-6-(1,2-Dihydroxy-1-methyl-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester
CAS No.:102991-13-9
Molecular Formula:C₁₉H₂₅NO₆S
Molecular Weight:395.477
Hs Code.:

Synonyms:(5R,6S)-6-(1,2-Dihydroxy-1-methyl-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

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Chemical Property of (5R,6S)-6-(1,2-Dihydroxy-1-methyl-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

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Technology Process of (5R,6S)-6-(1,2-Dihydroxy-1-methyl-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

There total 1 articles about (5R,6S)-6-(1,2-Dihydroxy-1-methyl-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl 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:

: 26205-43-6
O-trimethylsilylacetol

: 75722-79-1,102991-12-8
(5R,6S)-6-Iodo-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

: 102991-13-9
(5R,6S)-6-(1,2-Dihydroxy-1-methyl-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

Guidance literature:: With hydrogenchloride; methylmagnesium bromide; Yield given. Multistep reaction; 1.) ether, -70 degC; 2.) water/EtAc, 1 h, ice-cooling;
DOI:10.1248/cpb.33.4371

Reference yield: 52.0%

: 75-44-5
phosgene

: 102991-13-9
(5R,6S)-6-(1,2-Dihydroxy-1-methyl-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

: 103022-09-9,103024-54-0,103067-40-9
(5R,6S)-3,3-Dimethyl-6-(4-methyl-2-oxo-[1,3]dioxolan-4-yl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

Guidance literature:: With pyridine; In dichloromethane; toluene; at -30 - -10 ℃; for 1h;
DOI:10.1248/cpb.33.4371

Reference yield:

: 102991-13-9
(5R,6S)-6-(1,2-Dihydroxy-1-methyl-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxy-benzyl ester

: 97129-46-9
(5R,6S)-6-((R)-4-Methyl-2-oxo-[1,3]dioxolan-4-yl)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 52 percent / pyridine / CH₂Cl₂; toluene / 1 h / -30 - -10 °C

2: 70 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h / ice-cooling

3: 1.) trimethyl phosphite; 2.) triethylamine / 1.) toluene, reflux, 1 h; 2.) CH₂Cl₂, 30 min, room temperature

4: 1.) ozone; 2.) Zn, acetic acid / 1.) CH₂Cl₂/MeOH, -70 degC, 30 min; 2.) 30 min, ice-cooling

5: thionyl bromide, 2,6-lutidine / tetrahydrofuran / 0.5 h / -30 °C

6: 60 percent / 2,6-lutidine / dioxane / 0.17 h

7: 1.) AgClO₄; 2.) pyridine / 1.) dioxane, ice-cooling, 3 h; 2.) CH₂Cl₂, -40 degC, 1 h

8: toluene / 1.5 h / 60 °C

9: tetra-n-butylammonium bromide / CH₂Cl₂; H₂O / 2 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; dibromo sulfoxide; silver perchlorate; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; phosphorous acid trimethyl ester; tetrabutylammomium bromide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene;
DOI:10.1248/cpb.33.4371