(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

Base Information

• Chemical Name: (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
• CAS No.: 566198-54-7
• Molecular Formula: C₃₂H₄₇NO₇Si
• Molecular Weight: 585.813
• Mol file: 566198-54-7.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 7 articles about (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 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:

Benzophenone imine (1013-88-3) → (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 (566198-54-7)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: NaBH₃CN; AcOH / acetonitrile / 2 h

1.3: 74 percent / aq. NaBH₃CN; AcOH / 24 h

2.1: 2,6-lutidine / CH₂Cl₂ / 16 h

With 2,6-dimethylpyridine; hydrogenchloride; In methanol; dichloromethane;

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) → (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 (566198-54-7)

Guidance literature:

Multi-step reaction with 6 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

6.1: 2,6-lutidine / CH₂Cl₂ / 16 h

With 2,6-dimethylpyridine; 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:

(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) → (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 (566198-54-7)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: NaBH₃CN; AcOH / acetonitrile / 2 h

1.3: 74 percent / aq. NaBH₃CN; AcOH / 24 h

2.1: 2,6-lutidine / CH₂Cl₂ / 16 h

With 2,6-dimethylpyridine; hydrogenchloride; In methanol; dichloromethane;

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

upstream raw materials:

t-butyldimethylsiyl triflate

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

Benzophenone imine

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