H-Thr(Bzl)-OBzl

Base Information

• Chemical Name: H-Thr(Bzl)-OBzl
• CAS No.: 42001-91-2
• Molecular Formula: C₁₈H₂₁NO₃
• Molecular Weight: 299.37
• DSSTox Substance ID: DTXSID801242728
• Mol file: 42001-91-2.mol

Synonyms:H-Thr(Bzl)-OBzl;SCHEMBL5196444;JFGFSGAITLXWHG-PBHICJAKSA-N;DTXSID801242728;phenylmethyl O-(phenylmethyl)-L-threoninate;O-(Phenylmethyl)-L-threonine phenylmethyl ester;(2S,3R)-benzyl 2-amino-3-(benzyloxy)butanoate;42001-91-2

Chemical Property of H-Thr(Bzl)-OBzl

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 299.15214353
• Heavy Atom Count: 22
• Complexity: 322

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C(=O)OCC1=CC=CC=C1)N)OCC2=CC=CC=C2
• Isomeric SMILES: C[C@H]([C@@H](C(=O)OCC1=CC=CC=C1)N)OCC2=CC=CC=C2

Technology Process of H-Thr(Bzl)-OBzl

There total 2 articles about H-Thr(Bzl)-OBzl 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: 83.0%

N-Fmoc-O-benzyl-L-threonine benzyl ester (1353655-02-3) → (2S,3R)-benzyl 2-amino-3-(benzyloxy)butanoate oxalate (42001-91-2)

Guidance literature:

With piperidine; In dichloromethane; at 0 ℃; for 0.25h; Inert atmosphere;

DOI:10.1016/j.tet.2011.10.099

Reference yield:

N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester (73724-48-8) → (2S,3R)-benzyl 2-amino-3-(benzyloxy)butanoate oxalate (42001-91-2)

Guidance literature:

Multi-step reaction with 2 steps

1: silver(l) oxide / dichloromethane / 24 h / 20 °C / Inert atmosphere

2: piperidine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

With piperidine; silver(l) oxide; In dichloromethane;

DOI:10.1016/j.tet.2011.10.099

Reference yield: 94.0%

(2S,3R)-benzyl 2-amino-3-(benzyloxy)butanoate oxalate (42001-91-2) + chloroacetyl chloride (79-04-9) → Nα-(2-chloroacetyl)-O-benzyl-L-threonine benzyl ester

Guidance literature:

With potassium carbonate; In dichloromethane; at 0 ℃; for 2.5h; Reflux;

DOI:10.1093/nar/gkab026

upstream raw materials:

N-Fmoc-O-benzyl-L-threonine benzyl ester

N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester

Downstream raw materials:

N-(tert-butoxycarbonyl)valine-O-benzyl-L-threonine benzyl ester

O-benzyl-N-<(3S,6S)-2-benzyloxycarbonyl-6-carboxy-6-<(chloroacetamido)methyl>perhydro-1,2-oxazine-3-carbonyl>-L-threonine benzyl ester

(3R,6R)-3-((1S,2R)-2-Benzyloxy-1-benzyloxycarbonyl-propylcarbamoyl)-6-[(2-chloro-acetylamino)-methyl]-[1,2]oxazinane-2,6-dicarboxylic acid 2-benzyl ester

Boc-ST(OBn)3