(1R,4S,5S)-2-Oxo-4-(toluene-4-sulfonyloxymethyl)-3-oxa-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester

Base Information

• Chemical Name: (1R,4S,5S)-2-Oxo-4-(toluene-4-sulfonyloxymethyl)-3-oxa-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester
• CAS No.: 866944-19-6
• Molecular Formula: C₂₀H₁₉NO₇S
• Molecular Weight: 417.439
• Mol file: 866944-19-6.mol

Synonyms:(1R,4S,5S)-2-Oxo-4-(toluene-4-sulfonyloxymethyl)-3-oxa-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester

Chemical Property of (1R,4S,5S)-2-Oxo-4-(toluene-4-sulfonyloxymethyl)-3-oxa-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S,5S)-2-Oxo-4-(toluene-4-sulfonyloxymethyl)-3-oxa-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester

There total 2 articles about (1R,4S,5S)-2-Oxo-4-(toluene-4-sulfonyloxymethyl)-3-oxa-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid 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: 74.0%

(1S,2S,5R)-2-Hydroxymethyl-4-oxo-3-oxa-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester (866944-18-5) + p-toluenesulfonyl chloride (98-59-9) → (1R,4S,5S)-2-Oxo-4-(toluene-4-sulfonyloxymethyl)-3-oxa-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester (866944-19-6)

Guidance literature:

With pyridine; dmap; In dichloromethane; at -15 ℃; for 24h;

DOI:10.1021/ja052969z

Reference yield:

(1R,4S,5S)-6-(benzyloxycarbonyl)-4-[(tert-butyldiphenylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.1.0]hexan-2-one (639820-24-9) → (1R,4S,5S)-2-Oxo-4-(toluene-4-sulfonyloxymethyl)-3-oxa-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester (866944-19-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / TBAF / tetrahydrofuran / 2.5 h / -60 - 20 °C

2: 74 percent / 4-(dimethylamino)pyridine; pyridine / CH₂Cl₂ / 24 h / -15 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja052969z

Reference yield: 85.0%

(1R,4S,5S)-2-Oxo-4-(toluene-4-sulfonyloxymethyl)-3-oxa-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester (866944-19-6) → ((1S,4S,7R)-3-Oxo-2-oxa-5-thia-bicyclo[2.2.1]hept-7-yl)-carbamic acid benzyl ester

Guidance literature:

With benzyltriethylammonium tetrathiomolybdate; In acetonitrile; at 28 ℃; for 3h;

DOI:10.1021/ja052969z

upstream raw materials:

(1S,2S,5R)-2-Hydroxymethyl-4-oxo-3-oxa-6-aza-bicyclo[3.1.0]hexane-6-carboxylic acid benzyl ester

p-toluenesulfonyl chloride

(1R,4S,5S)-6-(benzyloxycarbonyl)-4-[(tert-butyldiphenylsilyloxy)methyl]-3-oxa-6-azabicyclo[3.1.0]hexan-2-one