benzyl N-[(2S)-2,3-dihydroxypropyl]carbamate

Base Information

• Chemical Name: benzyl N-[(2S)-2,3-dihydroxypropyl]carbamate
• CAS No.: 135582-93-3
• Molecular Formula: C11H15NO4
• Molecular Weight: 225.244
• DSSTox Substance ID: DTXSID001227689
• Mol file: 135582-93-3.mol

Synonyms:135582-93-3;benzyl N-[(2S)-2,3-dihydroxypropyl]carbamate;(S)-Benzyl (2,3-dihydroxypropyl)carbamate;SCHEMBL1568538;DAMJAHUBTRVKPI-JTQLQIEISA-N;DTXSID001227689;MFCD30569487;PS-15839;(S)-Benzyl(2,3-dihydroxypropyl)carbamate;CS-0309484;Benzyln-[(2s)-2,3-dihydroxypropyl]carbamate;P18186;EN300-7329410;(S)-2,3-Dihydroxy-1-propylcarbamate benzyl ester;Phenylmethyl N-[(2S)-2,3-dihydroxypropyl]carbamate

Chemical Property of benzyl N-[(2S)-2,3-dihydroxypropyl]carbamate

Chemical Property:

• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 225.10010796
• Heavy Atom Count: 16
• Complexity: 204

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NCC(CO)O
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)NC[C@@H](CO)O

Technology Process of benzyl N-[(2S)-2,3-dihydroxypropyl]carbamate

There total 3 articles about benzyl N-[(2S)-2,3-dihydroxypropyl]carbamate 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: 94.0%

(S)-4-benzyloxycarbonylaminomethyl-2,2-dimethyl-1,3-dioxolane (134038-71-4) → (S)-3-[N-(benzyloxycarbonyl)amino]-1,2-propanediol (135582-93-3)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; water; for 2h; Heating;

DOI:10.1055/s-1991-26480

Reference yield: 94.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + (S)-3-Amino-1,2-propanediol (61278-21-5,98923-21-8) → (S)-3-[N-(benzyloxycarbonyl)amino]-1,2-propanediol (135582-93-3)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; at 20 ℃;

DOI:10.1055/s-2003-40840

Reference yield: 85.0%

(S)-3-Amino-1,2-propanediol (61278-21-5,98923-21-8) + benzyl chloroformate (501-53-1,94274-21-2) → (S)-3-[N-(benzyloxycarbonyl)amino]-1,2-propanediol (135582-93-3)

Guidance literature:

With sodium hydrogencarbonate; In water; acetonitrile;

DOI:10.1021/ja073911i

upstream raw materials:

(S)-4-benzyloxycarbonylaminomethyl-2,2-dimethyl-1,3-dioxolane

N-(Benzyloxycarbonyloxy)succinimide

(S)-3-Amino-1,2-propanediol

benzyl chloroformate

Downstream raw materials:

(S)-3-benzyloxycarbonylamino-2-hydroxy-1-(o-nitrobenzoyloxy)propane

Toluene-4-sulfonic acid (S)-3-benzyloxycarbonylamino-2-hydroxy-propyl ester

(5S)-N-benzyloxycarbonyl-5-iodomethyl oxazolidine

(S)-2,2-Dimethyl-5-(toluene-4-sulfonyloxymethyl)-oxazolidine-3-carboxylic acid benzyl ester