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

Base Information

• Chemical Name: (2R,3R)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)-3-methoxy-3-phenylazetidin-3-ol
• CAS No.: 219676-54-7
• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.38
• Mol file: 219676-54-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about (2R,3R)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)-3-methoxy-3-phenylazetidin-3-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: 99.0%

(2R,3R)-1-(benzyloxycarbonyl)-2-<(dimethyl)(1,1,2-trimethylpropyl)silyloxymethyl>-3-methoxy-3-phenylazetidin-3-ol (219676-53-6) → (2R,3R)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)-3-methoxy-3-phenylazetidin-3-ol (219676-54-7)

Guidance literature:

With hydrogen fluoride; In acetonitrile; for 0.5h;

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) → (2R,3R)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)-3-methoxy-3-phenylazetidin-3-ol (219676-54-7)

Guidance literature:

Multi-step reaction with 12 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

5: 98 percent / imidazole / dimethylformamide / 40 °C

6: 79 percent / NaH / tetrahydrofuran

7: 89 percent / 40 percent aq. HF / acetonitrile

8: 97 percent / imidazole / dimethylformamide / 3 h

9: 60 percent / Dess-Martin periodination reagent / CH₂Cl₂ / 1 h

10: 80 percent / cyclohexane / 1 h / Irradiation

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

12: 99 percent / 40 percent aq. HF / acetonitrile / 0.5 h

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

Reference yield:

(R)-2-<(benzyloxycarbonyl)amino>-3-<(dimethyl)(1,1,2-trimethylpropyl)silyloxy>propanal (219676-46-7) → (2R,3R)-1-(benzyloxycarbonyl)-2-(hydroxymethyl)-3-methoxy-3-phenylazetidin-3-ol (219676-54-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 44 percent / tetrahydrofuran; diethyl ether / -78 deg C, 15 min; RT, 5 h

2: 98 percent / imidazole / dimethylformamide / 40 °C

3: 79 percent / NaH / tetrahydrofuran

4: 89 percent / 40 percent aq. HF / acetonitrile

5: 97 percent / imidazole / dimethylformamide / 3 h

6: 60 percent / Dess-Martin periodination reagent / CH₂Cl₂ / 1 h

7: 80 percent / cyclohexane / 1 h / Irradiation

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

9: 99 percent / 40 percent aq. HF / acetonitrile / 0.5 h

With 1H-imidazole; hydrogen fluoride; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; 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:

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

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

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

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

Downstream raw materials:

(2S,3R)-1-(benzyloxycarbonyl)-3-methoxy-3-phenylazetidine-2-carboxylic acid