methyl 3,5-di-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside

Base Information

• Chemical Name: methyl 3,5-di-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside
• CAS No.: 121250-70-2
• Molecular Formula: C₂₉H₃₁NO₆
• Molecular Weight: 489.568
• Mol file: 121250-70-2.mol

Synonyms:methyl 3,5-di-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside

Chemical Property of methyl 3,5-di-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,5-di-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside

There total 9 articles about methyl 3,5-di-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside 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:

6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose (20398-90-7) → (1R,4S,5R,8R)-4,8-Bis-benzyloxy-7-methoxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester (121195-22-0,121250-70-2,129212-19-7,129212-23-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / sodium hydride, tetrabutylammonium iodide / tetrahydrofuran

2: 67 percent / hydrogen chloride

4: tin(II)-chloride / methanol

5: sodium acetate / ethanol

With hydrogenchloride; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; tin(ll) chloride; In tetrahydrofuran; methanol; ethanol;

DOI:10.1016/S0040-4039(00)94568-4

Reference yield:

1,2-O-isopropylidene-3,5-di-O-benzyl-6-azido-6-deoxy-β-L-idofuranose (115351-18-3) → (1R,4S,5R,8R)-4,8-Bis-benzyloxy-7-methoxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester (121195-22-0,121250-70-2,129212-19-7,129212-23-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 67 percent / hydrogen chloride

3: tin(II)-chloride / methanol

4: sodium acetate / ethanol

With hydrogenchloride; sodium acetate; tin(ll) chloride; In methanol; ethanol;

DOI:10.1016/S0040-4039(00)94568-4

Reference yield:

Trifluoro-methanesulfonic acid (3R,4S,5R)-5-((S)-2-amino-1-benzyloxy-ethyl)-4-benzyloxy-2-methoxy-tetrahydro-furan-3-yl ester (128984-78-1,128984-79-2) → (1R,4S,5R,8R)-4,8-Bis-benzyloxy-7-methoxy-6-oxa-2-aza-bicyclo[3.2.1]octane-2-carboxylic acid benzyl ester (121195-22-0,121250-70-2,129212-19-7,129212-23-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium acetate / ethanol

With sodium acetate; In ethanol;

DOI:10.1016/S0040-4039(00)94568-4

upstream raw materials:

(1R,4S,5R,8R)-4,8-Bis-benzyloxy-7-methoxy-6-oxa-2-aza-bicyclo[3.2.1]octane

benzyl chloroformate

6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

1,2-O-isopropylidene-3,5-di-O-benzyl-6-azido-6-deoxy-β-L-idofuranose

Downstream raw materials:

1,5-dideoxy-1,5-imino-D-glucitol

N-benzyloxycarbonyl-2,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-glucitol

3,5-di-O-benzyl-N-benzyloxycarbonyl-2,6-dideoxy-2,6-imino-D-mannose

1-deoxymannojirimycin