(1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester

Base Information

• Chemical Name: (1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester
• CAS No.: 151074-57-6
• Molecular Formula: C₁₄H₁₇NO₅
• Molecular Weight: 279.293
• Mol file: 151074-57-6.mol

Synonyms:(1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester

Chemical Property of (1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester

There total 9 articles about (1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic 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: 87.0%

methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-formylcyclopropanecarboxylate (175694-63-0) → (1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester (151074-57-6)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h;

DOI:10.1016/0957-4166(96)00038-9

Reference yield: 83.0%

(1S,2R)-1-Amino-2-hydroxymethyl-cyclopropanecarboxylic acid methyl ester (114498-10-1) + benzyl chloroformate (501-53-1,94274-21-2) → (1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester (151074-57-6)

Guidance literature:

With sodium carbonate; at 0 ℃; for 4h;

DOI:10.1016/S0040-4020(01)80152-6

Reference yield:

methyl (4S,2Z)-2-benzyloxycarbonylamino-4,5-isopropylidenedioxy-2-pentanoate (132970-32-2) → (1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester (151074-57-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / diethyl ether / 4 h / Ambient temperature

2: 100 percent / benzophenone / CH₂Cl₂ / 0.3 h / -78 °C

3: 100 percent / 5percent HCl/MeOH / 2.5 h / Ambient temperature

4: 90 percent / tetrahydrofuran / 6 h / Heating

5: 90 percent / 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine / 20 h / 40 °C

6: 1.) O₃, 2.) Me₂S / 1.) AcOEt, -78 deg C, 20 min, 2.) AcOEt, RT, 30 min

7: 87 percent / NaBH₄ / methanol / 0.33 h / 0 °C

With 1,3-dimethyl-2-phenyl-1,3,2-diazaphospholidine; hydrogenchloride; methanol; sodium tetrahydroborate; benzophenone; dimethylsulfide; ozone; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1016/0957-4166(96)00038-9

upstream raw materials:

(1S,2R)-1-Amino-2-hydroxymethyl-cyclopropanecarboxylic acid methyl ester

benzyl chloroformate

methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-formylcyclopropanecarboxylate

N-(benzyloxycarbonyl)phosphonoglycine trimethyl ester

Downstream raw materials:

(1S,2S)-1-benzyloxycarbonylamino-2-(N-phthalimido)methyl-1-cyclopropanecarboxylic acid methyl ester

(1S,2S)-2-aminomethyl-1-benzyloxycarbonylamino-1-cyclopropanecarboxylic acid methyl ester

methyl (1S,2R)-(+)-1-N-benzyloxycarbonylamino-2-iodomethylcyclopropanecarboxylate

(-)-(Z)-2,3-methanomethionine