(1S,4R,5S,7S,8R)-8-Benzyloxy-7-methoxy-4-trifluoromethanesulfonyloxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester

Base Information

• Chemical Name: (1S,4R,5S,7S,8R)-8-Benzyloxy-7-methoxy-4-trifluoromethanesulfonyloxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester
• CAS No.: 113000-80-9
• Molecular Formula: C₂₃H₂₄F₃NO₈S
• Molecular Weight: 531.507
• Mol file: 113000-80-9.mol

Synonyms:(1S,4R,5S,7S,8R)-8-Benzyloxy-7-methoxy-4-trifluoromethanesulfonyloxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester

Chemical Property of (1S,4R,5S,7S,8R)-8-Benzyloxy-7-methoxy-4-trifluoromethanesulfonyloxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R,5S,7S,8R)-8-Benzyloxy-7-methoxy-4-trifluoromethanesulfonyloxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester

There total 10 articles about (1S,4R,5S,7S,8R)-8-Benzyloxy-7-methoxy-4-trifluoromethanesulfonyloxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-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:

trifluoromethylsulfonic anhydride (358-23-6) + methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside (98260-67-4) → (1S,4R,5S,7S,8R)-8-Benzyloxy-7-methoxy-4-trifluoromethanesulfonyloxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester (113000-80-9)

Guidance literature:

With pyridine; at -20 ℃; Yield given;

DOI:10.1016/S0040-4039(00)99073-7

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose-5,6-carbonate (16895-86-6) → (1S,4R,5S,7S,8R)-8-Benzyloxy-7-methoxy-4-trifluoromethanesulfonyloxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester (113000-80-9)

Guidance literature:

Multi-step reaction with 7 steps

1: methanol / Dowex 50W-X₈ resin (H⁺ form) / Heating

2: pyridine / CH₂Cl₂ / 0.33 h / -20 °C

3: NaN₃ / dimethylformamide / 48 h / 50 °C

4: methanol / sodium methylate / Ambient temperature

5: pyridine / 6 h / Ambient temperature

7: pyridine / -20 °C

With pyridine; methanol; sodium azide; Dowex 50W-X₈ resin (H⁺ form); sodium methylate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)99073-7

Reference yield:

methyl-3-O-benzyl-α-D-glucofuranoside-5,6-carbonate (16895-87-7) → (1S,4R,5S,7S,8R)-8-Benzyloxy-7-methoxy-4-trifluoromethanesulfonyloxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester (113000-80-9)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / CH₂Cl₂ / 0.33 h / -20 °C

2: NaN₃ / dimethylformamide / 48 h / 50 °C

3: methanol / sodium methylate / Ambient temperature

4: pyridine / 6 h / Ambient temperature

6: pyridine / -20 °C

With pyridine; methanol; sodium azide; sodium methylate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)99073-7

upstream raw materials:

trifluoromethylsulfonic anhydride

methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside

3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose-5,6-carbonate

methyl-3-O-benzyl-α-D-glucofuranoside-5,6-carbonate

Downstream raw materials:

(1R,4S,5S,7R,8R)-4-Acetylamino-8-benzyloxy-7-methoxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester

(1R,4R,5S,7R,8R)-4-Acetylamino-8-benzyloxy-7-methoxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester

(2R,3R,4R,5R)-5-Acetylamino-3-benzyloxy-4-hydroxy-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

2-acetamido-N-benzyloxycarbonyl-4-O-benzyl-1,5-imino-1,2,5-trideoxy-D-glucitol