Methyl-3-azido-2-O-benzoyl-4,6-O-benzyliden-3-desoxy-α-D-glucopyranosid

Base Information

• Chemical Name: Methyl-3-azido-2-O-benzoyl-4,6-O-benzyliden-3-desoxy-α-D-glucopyranosid
• CAS No.: 88425-05-2
• Molecular Formula: C₂₁H₂₁N₃O₆
• Molecular Weight: 411.414
• Mol file: 88425-05-2.mol

Synonyms:Methyl-3-azido-2-O-benzoyl-4,6-O-benzyliden-3-desoxy-α-D-glucopyranosid

Chemical Property of Methyl-3-azido-2-O-benzoyl-4,6-O-benzyliden-3-desoxy-α-D-glucopyranosid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl-3-azido-2-O-benzoyl-4,6-O-benzyliden-3-desoxy-α-D-glucopyranosid

There total 2 articles about Methyl-3-azido-2-O-benzoyl-4,6-O-benzyliden-3-desoxy-α-D-glucopyranosid 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: 97.0%

Methyl-2-O-benzoyl-4,6-O-benzyliden-3-O-trifluormethylsulfonyl-α-D-allopyranosid (99679-77-3) → Methyl-3-azido-2-O-benzoyl-4,6-O-benzyliden-3-desoxy-α-D-glucopyranosid (88425-05-2)

Guidance literature:

With lithium azide; In dimethyl sulfoxide; N,N-dimethyl-formamide; 1.) 30 min, r.t.; 2.) 30 min, 50 degC;

Reference yield:

(2R,4aR,6S,7R,8R,8aR)-8-hydroxy-6-methoxy-2-phenyl-7-phenylcarbonyloxyperhydropyrano[3,2-d][1,3]dioxine (99265-94-8) → Methyl-3-azido-2-O-benzoyl-4,6-O-benzyliden-3-desoxy-α-D-glucopyranosid (88425-05-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / CH₂Cl₂; pyridine / 5 h / Ambient temperature

2: 97 percent / LiN₃ / dimethylsulfoxide; dimethylformamide / 1.) 30 min, r.t.; 2.) 30 min, 50 degC

With lithium azide; In pyridine; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

Methyl-3-azido-2-O-benzoyl-4,6-O-benzyliden-3-desoxy-α-D-glucopyranosid (88425-05-2) → Methyl-3-<(benzyloxycarbonyl)amino>-3,4-didesoxy-α-D-glycero-hex-3-enopyranosid-2-ulose (99679-92-2)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 86 percent / NaHCO₃ / H₂O; acetone / 0.5 h / 0 °C

3: 81 percent / CrO₃, pyridine, acetanhydride / CH₂Cl₂ / 0.42 h / Ambient temperature

4: 74 percent / LDA / tetrahydrofuran / 1 h / -78 °C

With pyridine; chromium(VI) oxide; hydrogen; sodium methylate; acetic anhydride; sodium hydrogencarbonate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; acetone;

upstream raw materials:

Methyl-2-O-benzoyl-4,6-O-benzyliden-3-O-trifluormethylsulfonyl-α-D-allopyranosid

(2R,4aR,6S,7R,8R,8aR)-8-hydroxy-6-methoxy-2-phenyl-7-phenylcarbonyloxyperhydropyrano[3,2-d][1,3]dioxine

Downstream raw materials:

methyl 3-amino-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside

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

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