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

Base Information

• Chemical Name: Methyl-3-<(benzyloxycarbonyl)amino>-3,4-didesoxy-α-D-glycero-hex-3-enopyranosid-2-ulose
• CAS No.: 99679-92-2
• Molecular Formula: C₁₅H₁₇NO₆
• Molecular Weight: 307.303
• Mol file: 99679-92-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about Methyl-3-<(benzyloxycarbonyl)amino>-3,4-didesoxy-α-D-glycero-hex-3-enopyranosid-2-ulose 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: 74.0%

Methyl-4,6-O-benzyliden-3-<(benzyloxycarbonyl)amino>-3-desoxy-α-D-arabino-hexopyranosid-2-ulose (99679-78-4) → Methyl-3-<(benzyloxycarbonyl)amino>-3,4-didesoxy-α-D-glycero-hex-3-enopyranosid-2-ulose (99679-92-2)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 1h;

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-3-<(benzyloxycarbonyl)amino>-3,4-didesoxy-α-D-glycero-hex-3-enopyranosid-2-ulose (99679-92-2)

Guidance literature:

Multi-step reaction with 6 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

5: CrO₃, pyridine

6: 74 percent / LDA / tetrahydrofuran / 1 h / -78 °C

With pyridine; chromium(VI) oxide; lithium azide; hydrogen; sodium methylate; sodium hydrogencarbonate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

Reference yield:

methyl 3-azido-3-deoxy-4,6-O-(phenylmethylene)-2-benzoate-α-D-allopyranoside (99745-47-8) → 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: 85 percent / NaHCO₃ / H₂O; acetone / 0.5 h / 0 °C

3: CrO₃, pyridine

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

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

upstream 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 iodide

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