Methyl-4,6-O-benzyliden-3-<(benzyloxycarbonyl)amino>-3-desoxy-α-D-allopyranosid

Base Information

• Chemical Name: Methyl-4,6-O-benzyliden-3-<(benzyloxycarbonyl)amino>-3-desoxy-α-D-allopyranosid
• CAS No.: 99745-49-0
• Molecular Formula: C₂₂H₂₅NO₇
• Molecular Weight: 415.443
• Mol file: 99745-49-0.mol

Synonyms:Methyl-4,6-O-benzyliden-3-<(benzyloxycarbonyl)amino>-3-desoxy-α-D-allopyranosid

Chemical Property of Methyl-4,6-O-benzyliden-3-<(benzyloxycarbonyl)amino>-3-desoxy-α-D-allopyranosid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl-4,6-O-benzyliden-3-<(benzyloxycarbonyl)amino>-3-desoxy-α-D-allopyranosid

There total 4 articles about Methyl-4,6-O-benzyliden-3-<(benzyloxycarbonyl)amino>-3-desoxy-α-D-allopyranosid 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: 85.0%

Methyl-3-amino-4,6-O-benzyliden-3-desoxy-α-D-allopyranosid (99745-48-9) + benzyl chloroformate (501-53-1,94274-21-2) → Methyl-4,6-O-benzyliden-3-<(benzyloxycarbonyl)amino>-3-desoxy-α-D-allopyranosid (99745-49-0)

Guidance literature:

With sodium hydrogencarbonate; In water; acetone; at 0 ℃; for 0.5h;

Reference yield:

methyl 4,6-O-(phenylmethylene)-2-benzoate-3-(trifluoromethanesulfonate)-α-D-glucopyranoside (99679-79-5) → Methyl-4,6-O-benzyliden-3-<(benzyloxycarbonyl)amino>-3-desoxy-α-D-allopyranosid (99745-49-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / LiN₃ / dimethylsulfoxide; dimethylformamide / 4.5 h / 50 °C

2: 1.) 1percent NaOMe; 2.) H₂ / 2.) 10percent Pd/C / 1.) CH₃OH, 4 h, r.t.; 2.) CH₃OH, 18 h

3: 85 percent / NaHCO₃ / H₂O; acetone / 0.5 h / 0 °C

With lithium azide; hydrogen; sodium methylate; sodium hydrogencarbonate; palladium on activated charcoal; In water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

Reference yield:

methyl 2-O-benzoyl-4,6-di-O-benzylidene-α-D-glucopyranoside (28642-64-0,35823-97-3,38992-99-3,51591-23-2,55169-75-0,56253-26-0,72659-78-0,80041-30-1,80299-59-8,86420-70-4,86420-72-6,91685-06-2,99265-94-8,109010-33-5,118246-05-2,126255-07-0) → Methyl-4,6-O-benzyliden-3-<(benzyloxycarbonyl)amino>-3-desoxy-α-D-allopyranosid (99745-49-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / CH₂Cl₂; pyridine / 5 h / Ambient temperature

2: 68 percent / LiN₃ / dimethylsulfoxide; dimethylformamide / 4.5 h / 50 °C

3: 1.) 1percent NaOMe; 2.) H₂ / 2.) 10percent Pd/C / 1.) CH₃OH, 4 h, r.t.; 2.) CH₃OH, 18 h

4: 85 percent / NaHCO₃ / H₂O; acetone / 0.5 h / 0 °C

With lithium azide; hydrogen; sodium methylate; sodium hydrogencarbonate; palladium on activated charcoal; In pyridine; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

upstream raw materials:

Methyl-3-amino-4,6-O-benzyliden-3-desoxy-α-D-allopyranosid

benzyl chloroformate

methyl 3-azido-3-deoxy-4,6-O-(phenylmethylene)-2-benzoate-α-D-allopyranoside

methyl 4,6-O-(phenylmethylene)-2-benzoate-3-(trifluoromethanesulfonate)-α-D-glucopyranoside

Downstream raw materials:

Methyl-4,6-O-benzyliden-3-<(benzyloxycarbonyl)amino>-3-desoxy-α-D-arabino-hexopyranosid-2-ulose

Methyl-4,6-O-benzyliden-3-<(benzyloxycarbonyl)amino>-3-desoxy-α-D-ribo-hexopyranosid-2-ulose

Methyl-3-<(benzyloxycarbonyl)amino>-3,4-didesoxy-α-D-glycero-hex-3-enopyranosid-2-ulose

Methyl-4,6-O-benzyliden-3-<(benzyloxycarbonyl)amino>-3-desoxy-3-C-methyl-α-D-arabino-hexopyranosid-2-ulose