(1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane-5-carboxylic acid benzyl ester

Base Information

• Chemical Name: (1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane-5-carboxylic acid benzyl ester
• CAS No.: 94119-07-0
• Molecular Formula: C₂₉H₃₁NO₆
• Molecular Weight: 489.568
• Mol file: 94119-07-0.mol

Synonyms:(1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane-5-carboxylic acid benzyl ester

Chemical Property of (1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane-5-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane-5-carboxylic acid benzyl ester

There total 11 articles about (1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane-5-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: 83.0%

(1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane (94119-06-9) + benzyl chloroformate (501-53-1,94274-21-2) → (1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane-5-carboxylic acid benzyl ester (94119-07-0)

Guidance literature:

With sodium hydrogencarbonate; In water; ethyl acetate;

DOI:10.1016/0040-4039(84)80058-1

Reference yield: 79.0%

Methanesulfonic acid (2R,3S,4S,5S,6S)-5-amino-4-benzyloxy-3-benzyloxymethyl-6-methoxy-tetrahydro-pyran-2-yl ester → (1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane-5-carboxylic acid benzyl ester (94119-07-0)

Guidance literature:

In N,N-dimethyl-formamide; at 50 ℃;

DOI:10.1016/0040-4039(84)80058-1

Reference yield:

methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside (76419-48-2) → (1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane-5-carboxylic acid benzyl ester (94119-07-0)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine / CH₂Cl₂ / -15 °C

2: NaN₃ / dimethylformamide / 60 °C

3: MeCOOH, H₂O

4: 89 percent / pyridine

5: 77 percent / Ag₂O / dimethylformamide / Ambient temperature

6: H₂ / Pd/C / ethyl acetate

7: 79 percent / dimethylformamide / 96 h / 50 °C

8: 83 percent / NaHCO₃ / ethyl acetate; H₂O

With pyridine; sodium azide; water; hydrogen; sodium hydrogencarbonate; acetic acid; silver(l) oxide; palladium on activated charcoal; In dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(84)80058-1

upstream raw materials:

(1R,3S,4S,7R,8R)-7,8-Bis-benzyloxy-3-methoxy-2-oxa-5-aza-bicyclo[2.2.2]octane

benzyl chloroformate

methyl 3,4-di-O-benzyl-α-D-glucopyranoside

methyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside

Downstream raw materials:

1-deoxymannojirimycin

3,4-di-O-benzyl-1,5-dideoxy-1,5-imino-D-mannitol