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

Base Information

• Chemical Name: methyl (R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>propanoate
• CAS No.: 219676-45-6
• Molecular Formula: C₂₀H₃₃NO₅Si
• Molecular Weight: 395.571
• Mol file: 219676-45-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about methyl (R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>propanoate 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: 99.0%

(R)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxypropanoate (93204-36-5) + chlorodimethyl(1,1,2-trimethylpropyl)silane (67373-56-2) → methyl (R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>propanoate (219676-45-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 3h;

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

Reference yield: 93.0%

methyl (R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>propanoate (219676-45-6) → (S)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>propan-1-ol (154657-60-0)

Guidance literature:

With sodium tetrahydroborate; In methanol;

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

Reference yield:

methyl (R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>propanoate (219676-45-6) → (2R,3R)-1-(benzyloxycarbonyl)-2-<(dimethyl)(1,1,2-trimethylpropyl)silyloxymethyl>-3-methoxy-3-phenylazetidin-3-ol (219676-53-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 93 percent / NaBH₄ / methanol

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

3: 44 percent / tetrahydrofuran; diethyl ether / -78 deg C, 15 min; RT, 5 h

4: 98 percent / imidazole / dimethylformamide / 40 °C

5: 79 percent / NaH / tetrahydrofuran

6: 89 percent / 40 percent aq. HF / acetonitrile

7: 97 percent / imidazole / dimethylformamide / 3 h

8: 60 percent / Dess-Martin periodination reagent / CH₂Cl₂ / 1 h

9: 80 percent / cyclohexane / 1 h / Irradiation

10: 1) NaH (80 percent in oil) / 1) DMF, 1 h, -30 deg C, 2) DMF, RT, overnight

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

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

upstream raw materials:

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

chlorodimethyl(1,1,2-trimethylpropyl)silane

Downstream raw materials:

(S)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>propan-1-ol

(1R,2R)-2-<(benzyloxycarbonyl)(methyl)amino>-1-phenylpropane-1,3-diol

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

(2R,3R)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)-3-methoxy-3-phenylazetidin-3-ol