(1R,2R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>-1-phenylpropan-1-ol

Base Information

• Chemical Name: (1R,2R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>-1-phenylpropan-1-ol
• CAS No.: 219676-47-8
• Molecular Formula: C₂₅H₃₇NO₄Si
• Molecular Weight: 443.659
• Mol file: 219676-47-8.mol

Synonyms:(1R,2R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>-1-phenylpropan-1-ol

Chemical Property of (1R,2R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>-1-phenylpropan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>-1-phenylpropan-1-ol

There total 5 articles about (1R,2R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>-1-phenylpropan-1-ol 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: 44.0%

phenylmagnesium bromide (100-58-3) + (R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>propanal (219676-46-7) → (1R,2R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>-1-phenylpropan-1-ol (219676-47-8)

Guidance literature:

In tetrahydrofuran; diethyl ether; -78 deg C, 15 min; RT, 5 h;

DOI:10.1002/(SICI)1522-2675(19981007)81:10<1803::AID-HLCA1803>3.0.CO;2-4

Reference yield:

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate (93204-36-5) → (1R,2R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>-1-phenylpropan-1-ol (219676-47-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / imidazole / dimethylformamide / 3 h

2: 93 percent / NaBH₄ / methanol

3: Dess-Martin periodination reagent / CH₂Cl₂ / 1 h

4: 44 percent / tetrahydrofuran; diethyl ether / -78 deg C, 15 min; RT, 5 h

With 1H-imidazole; sodium tetrahydroborate; Dess-Martin periodane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1522-2675(19981007)81:10<1803::AID-HLCA1803>3.0.CO;2-4

Reference yield:

chlorodimethyl(1,1,2-trimethylpropyl)silane (67373-56-2) → (1R,2R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>-1-phenylpropan-1-ol (219676-47-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / imidazole / dimethylformamide / 3 h

2: 93 percent / NaBH₄ / methanol

3: Dess-Martin periodination reagent / CH₂Cl₂ / 1 h

4: 44 percent / tetrahydrofuran; diethyl ether / -78 deg C, 15 min; RT, 5 h

With 1H-imidazole; sodium tetrahydroborate; Dess-Martin periodane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1522-2675(19981007)81:10<1803::AID-HLCA1803>3.0.CO;2-4

upstream raw materials:

phenylmagnesium bromide

(R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>propanal

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate

chlorodimethyl(1,1,2-trimethylpropyl)silane

Downstream raw materials:

(1R,2R)-2-<(benzyloxycarbonyl)amino>-1-<(tertbutyl)(dimethyl)silyloxy>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>-1-phenylpropane

(1R,2R)-2-<(benzyloxycarbonyl)(methyl)amino>-1-<(tert-butyl)(dimethyl)silyloxy>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>-1-phenylpropane

(2R,3R)-1-(benzyloxycarbonyl)-2-<(dimethyl)(1,1,2-trimethylpropyl)silyloxymethyl>-3-phenylazetidin-3-ol

(2R,3R)-1-(benzyloxycarbonyl)-2-<(dimethyl)(1,1,2-trimethylpropyl)silyloxymethyl>-3-methoxy-3-phenylazetidin-3-ol