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

Base Information

• Chemical Name: methyl (methyl 6-deoxy-2,3-O-isopropylidene-6-[(N-benzhydryl-N-methyl)amino]-D-glycero-β-D-allo-heptafuranosid)uronate
• CAS No.: 566198-53-6
• Molecular Formula: C₂₆H₃₃NO₇
• Molecular Weight: 471.551
• Mol file: 566198-53-6.mol

Synonyms:

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

There total 6 articles about methyl (methyl 6-deoxy-2,3-O-isopropylidene-6-[(N-benzhydryl-N-methyl)amino]-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: 74.0%

Benzophenone imine (1013-88-3) + formaldehyd (50-00-0,30525-89-4,61233-19-0) + (2S,3R)-2-Amino-3-hydroxy-3-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionic acid methyl ester (147600-20-2) → methyl (methyl 6-deoxy-2,3-O-isopropylidene-6-[(N-benzhydryl-N-methyl)amino]-D-glycero-β-D-allo-heptafuranosid)uronate (566198-53-6)

Guidance literature:

Benzophenone imine; (2S,3R)-2-Amino-3-hydroxy-3-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionic acid methyl ester; With hydrogenchloride; In methanol; dichloromethane; for 24h;

With sodium cyanoborohydride; acetic acid; In acetonitrile; for 2h;

formaldehyd; With sodium cyanoborohydride; acetic acid; for 24h;

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

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-2,3-O-isopropylidene-6-[(N-benzhydryl-N-methyl)amino]-D-glycero-β-D-allo-heptafuranosid)uronate (566198-53-6)

Guidance literature:

Multi-step reaction with 5 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

4.1: 75 percent / H₂; Raney-Ni / methanol / 24 h / 760 Torr

5.1: satd. HCl / CH₂Cl₂; methanol / 24 h

5.2: NaBH₃CN; AcOH / acetonitrile / 2 h

5.3: 74 percent / aq. NaBH₃CN; AcOH / 24 h

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

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

Reference yield:

methyl (methyl 6-deoxy-2,3-O-isopropylidene-α-L-talo-heptofuranosid)yronate (168102-86-1) → methyl (methyl 6-deoxy-2,3-O-isopropylidene-6-[(N-benzhydryl-N-methyl)amino]-D-glycero-β-D-allo-heptafuranosid)uronate (566198-53-6)

Guidance literature:

Multi-step reaction with 3 steps

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

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

1.3: 56 percent / tetrahydrofuran / -78 °C

2.1: 75 percent / H₂; Raney-Ni / methanol / 24 h / 760 Torr

3.1: satd. HCl / CH₂Cl₂; methanol / 24 h

3.2: NaBH₃CN; AcOH / acetonitrile / 2 h

3.3: 74 percent / aq. NaBH₃CN; AcOH / 24 h

With hydrogenchloride; hydrogen; nickel; zinc methyl bromide; In tetrahydrofuran; methanol; dichloromethane;

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

upstream raw materials:

Benzophenone imine

formaldehyd

(2S,3R)-2-Amino-3-hydroxy-3-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-propionic acid methyl ester

(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