methyl (methyl 6-deoxy-6-N,N'-dibenzyloxycarbonylhydrazino-2,3-O-isopropylidene-D-glycero-β-D-allo-heptafuranosid)uronate

Base Information

• Chemical Name: methyl (methyl 6-deoxy-6-N,N'-dibenzyloxycarbonylhydrazino-2,3-O-isopropylidene-D-glycero-β-D-allo-heptafuranosid)uronate
• CAS No.: 566198-55-8
• Molecular Formula: C₂₈H₃₄N₂O₁₁
• Molecular Weight: 574.585
• Mol file: 566198-55-8.mol

Synonyms:methyl (methyl 6-deoxy-6-N,N'-dibenzyloxycarbonylhydrazino-2,3-O-isopropylidene-D-glycero-β-D-allo-heptafuranosid)uronate

Chemical Property of methyl (methyl 6-deoxy-6-N,N'-dibenzyloxycarbonylhydrazino-2,3-O-isopropylidene-D-glycero-β-D-allo-heptafuranosid)uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (methyl 6-deoxy-6-N,N'-dibenzyloxycarbonylhydrazino-2,3-O-isopropylidene-D-glycero-β-D-allo-heptafuranosid)uronate

There total 4 articles about methyl (methyl 6-deoxy-6-N,N'-dibenzyloxycarbonylhydrazino-2,3-O-isopropylidene-D-glycero-β-D-allo-heptafuranosid)uronate 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: 56.0%

dibenzyl azodicarboxylate (2449-05-0) + methyl (methyl 6-deoxy-2,3-O-isopropylidene-α-L-talo-heptofuranosid)yronate (168102-86-1) → methyl (methyl 6-deoxy-6-N,N'-dibenzyloxycarbonylhydrazino-2,3-O-isopropylidene-D-glycero-β-D-allo-heptafuranosid)uronate (566198-55-8)

Guidance literature:

methyl (methyl 6-deoxy-2,3-O-isopropylidene-α-L-talo-heptofuranosid)yronate; With zinc methyl bromide; In tetrahydrofuran; at 0 ℃; for 0.5h;

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

dibenzyl azodicarboxylate; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(03)00460-X

Reference yield: 56.0%

dibenzyl azodicarboxylate (2449-05-0) + methyl (methyl 6-deoxy-2,3-O-isopropylidene-β-D-allo-heptofuranosid)uronate (99441-06-2) → methyl (methyl 6-deoxy-6-N,N'-dibenzyloxycarbonylhydrazino-2,3-O-isopropylidene-D-glycero-β-D-allo-heptafuranosid)uronate (566198-55-8)

Guidance literature:

methyl (methyl 6-deoxy-2,3-O-isopropylidene-β-D-allo-heptofuranosid)uronate; With zinc methyl bromide; In tetrahydrofuran; at 0 ℃; for 1h;

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

dibenzyl azodicarboxylate; In tetrahydrofuran; at -78 ℃; for 1.5h; Further stages.;

DOI:10.1016/j.tetasy.2007.07.023

Reference yield:

(3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid (54622-95-6) → methyl (methyl 6-deoxy-6-N,N'-dibenzyloxycarbonylhydrazino-2,3-O-isopropylidene-D-glycero-β-D-allo-heptafuranosid)uronate (566198-55-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Im₂CO / tetrahydrofuran / 16 h / 20 °C

1.2: 60 percent / tetrahydrofuran / 16 h

2.1: 100 percent / H₂; RuBr₂[(S)-Binap] / methanol / 16 h / 40 °C / 760 Torr

3.1: MeZnBr / tetrahydrofuran / 0.5 h / 0 °C

3.2: LDA / tetrahydrofuran / 1 h / -78 °C

3.3: 56 percent / tetrahydrofuran / -78 °C

With (S)-BinapRuBr₂; hydrogen; 1,1'-carbonyldiimidazole; zinc methyl bromide; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(03)00460-X

upstream raw materials:

dibenzyl azodicarboxylate

methyl (methyl 6-deoxy-2,3-O-isopropylidene-α-L-talo-heptofuranosid)yronate

methyl (methyl 6-deoxy-2,3-O-isopropylidene-β-D-allo-heptofuranosid)uronate

(3aS,4S,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxylic acid

Downstream raw materials:

(2S,3R)-2-(Benzhydryl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-3-((3aR,4S,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionic acid methyl ester

methyl (methyl 6-deoxy-2,3-O-isopropylidene-6-[(N-benzhydryl-N-methyl)amino]-D-glycero-β-D-allo-heptafuranosid)uronate