(2S,3R,5R,6R)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-3-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (2S,3R,5R,6R)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-3-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 187155-32-4
• Molecular Formula: C₃₄H₄₁NO₇SSi
• Molecular Weight: 635.854

Synonyms:

Chemical Property of (2S,3R,5R,6R)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-3-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of (2S,3R,5R,6R)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-3-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

There total 1 articles about (2S,3R,5R,6R)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-3-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl 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-{(2R,3R)-2-(Benzothiazol-2-yldisulfanyl)-3-[(R)-(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid benzhydryl ester → (2S,3R,5R,6R)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-3-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (187155-32-4)

Guidance literature:

With potassium permanganate; silver(I) acetate; thiourea; chloroacetic acid; Multistep reaction; 1.) CH₂Cl₂, room temperature, 16 h, 2.) acetone, H₂O, glacial acetic acid, 3.) ethanol, 60 deg C, 70 min;

DOI:10.1016/S0960-894X(96)00575-6

Reference yield:

(2S,3R,5R,6R)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-3-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (187155-32-4) → (2S,3R,5R,6R)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-3-formyl-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (187155-33-5)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1016/S0960-894X(96)00575-6

Reference yield:

(2S,3R,5R,6R)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-3-hydroxymethyl-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (187155-32-4) → (2S,3R,5R,6R)-6-((R)-Hydroxy-phenyl-methyl)-3-(methoxyimino-methyl)-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (187155-35-7)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridinium chlorochromate / CH₂Cl₂ / 24 h / Ambient temperature

2: 58 percent / pyridine / CH₂Cl₂; ethanol

3: 60 percent / 48percent HF / acetonitrile / 1 h / Ambient temperature

With pyridine; hydrogen fluoride; pyridinium chlorochromate; In ethanol; dichloromethane; acetonitrile;

DOI:10.1016/S0960-894X(96)00575-6

Downstream raw materials:

(2S,3R,5R,6R)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-3-formyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

(2S,3R,5R,6R)-6-((R)-Hydroxy-phenyl-methyl)-3-(methoxyimino-methyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

(2S,3R,5R,6R)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-3-(methoxyimino-methyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

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