N-Boc-(S)-2-amino-3-benzyloxy-1-propanol

Base Information

• Chemical Name: N-Boc-(S)-2-amino-3-benzyloxy-1-propanol
• CAS No.: 79069-15-1
• Molecular Formula: C15H23NO4
• Molecular Weight: 281.352
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID80560157
• Nikkaji Number: J2.043.752I
• Wikidata: Q72447843
• Mol file: 79069-15-1.mol

Synonyms:79069-15-1;N-Boc-(S)-2-amino-3-benzyloxy-1-propanol;(S)-tert-Butyl (1-(benzyloxy)-3-hydroxypropan-2-yl)carbamate;Boc-Serinol(Bzl);tert-Butyl (S)-(1-(benzyloxy)-3-hydroxypropan-2-yl)carbamate;tert-butyl N-[(2S)-1-hydroxy-3-phenylmethoxypropan-2-yl]carbamate;(S)-2-(Boc-amino)-3-benzyloxy-1-propanol;(S)-tert-butyl 1-(benzyloxy)-3-hydroxypropan-2-ylcarbamate;MFCD00235945;SCHEMBL212797;DTXSID80560157;MSIDLARYVJJEQY-ZDUSSCGKSA-N;AKOS015836451;AKOS015890204;BS-49550;CS-0169628;Boc-(S)-2-Amino-3-Phenylmethoxy-1-Propanol;N-(tert-Butyloxycarbonyl)-O-Benzyl-D-Serinol;C76529;EN300-7303861;A839570;1-benzyloxy-2(S)-t-butoxycarbonylamino-3-hydroxypropane;tert-Butyl [(2S)-1-(benzyloxy)-3-hydroxypropan-2-yl]carbamate;tert-butyl N-[(2S)-1-(benzyloxy)-3-hydroxypropan-2-yl]carbamate;tert-butyl N-[(1S)-1-(benzyloxymethyl)-2-hydroxy-ethyl]carbamate

Chemical Property of N-Boc-(S)-2-amino-3-benzyloxy-1-propanol

Chemical Property:

• Melting Point: 66-69 °C(lit.)
• Boiling Point: 443.1±40.0 °C(Predicted)
• PKA: 11.58±0.46(Predicted)
• PSA: 67.79000
• Density: 1.105
• LogP: 2.47970
• Storage Temp.: Store at 0-5°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 281.16270821
• Heavy Atom Count: 20
• Complexity: 282

Purity/Quality:

99%+, ^*data from raw suppliers

Boc-O-benzyl-D-serinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CO)COCC1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CO)COCC1=CC=CC=C1

Technology Process of N-Boc-(S)-2-amino-3-benzyloxy-1-propanol

There total 53 articles about N-Boc-(S)-2-amino-3-benzyloxy-1-propanol 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: 98.0%

methyl O-benzyl-N-(tert-butoxycarbonyl)-L-serinate (80963-10-6) → N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol (79069-15-1)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; for 12h; Ambient temperature;

DOI:10.1055/s-1997-3186

Reference yield: 95.0%

(R)-3-benzyloxy-2-tert-butoxycarbonyl-amino-propionic acid methyl ester (67389-47-3) → tert-butyl N-[(1S)-1-(benzyloxymethyl)-2-hydroxy-ethyl]carbamate (79069-15-1)

Guidance literature:

With sodium tetrahydroborate; lithium chloride; In tetrahydrofuran; methanol; for 2h; Ambient temperature;

DOI:10.1021/jo961408a

Reference yield: 92.0%

N-Boc-D-serine(Bzl)-OH (47173-80-8) → tert-butyl N-[(1S)-1-(benzyloxymethyl)-2-hydroxy-ethyl]carbamate (79069-15-1)

Guidance literature:

N-Boc-D-serine(Bzl)-OH; With triethylamine; isobutyl chloroformate; In 1,2-dimethoxyethane; at 0 ℃; for 0.166667h;

With sodium tetrahydroborate; In methanol; 1,2-dimethoxyethane; at 0 ℃; for 0.333333h; Further stages.;

DOI:10.1016/j.tetasy.2007.10.004

upstream raw materials:

BOC-O-benzyl-L-serine

C₂₀H₂₉NO₇

methyl O-benzyl-N-(tert-butoxycarbonyl)-L-serinate

(S)-2-(t-butoxycarbonylamino)-3-phenylmetoxy-1-propanal

Downstream raw materials:

Succinic acid mono-((S)-3-benzyloxy-2-tert-butoxycarbonylamino-propyl) ester

(S)-2-t-butoxycarbonylamino-3-benzyloxy-1-methanesulfonyloxypropane

(R)-2-t-butoxycarbonylamino-3-benzyloxy-1-methanesulfonyloxypropane

(R)-2-[(S)-3-(3-Benzoyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-tert-butoxycarbonylamino-propoxy]-propionic acid tert-butyl ester

Refernces

• 1、 -. "DEUTERATED COMPOUNDS FOR USE IN THE TREATMENT OF CANCER". . . Retrieved 2021/02/19.
• 2、 -. "LPA5 RECEPTOR AGONIST". Paragraph 0219; 0220. . Retrieved 2018/07/31.