Boc-Ser(PO3Bzl2)-OH

Base Information

• Chemical Name: Boc-Ser(PO3Bzl2)-OH
• CAS No.: 90013-45-9
• Molecular Formula: C22H28 N O8 P
• Molecular Weight: 465.44
• DSSTox Substance ID: DTXSID80564458
• Mol file: 90013-45-9.mol

Synonyms:Boc-Ser(PO3Bzl2)-OH;90013-45-9;(S)-3-((Bis(benzyloxy)phosphoryl)oxy)-2-((tert-butoxycarbonyl)amino)propanoic acid;(2S)-3-bis(phenylmethoxy)phosphoryloxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid;SCHEMBL17471771;DTXSID80564458;(2S)-3-{[bis(benzyloxy)phosphoryl]oxy}-2-{[(tert-butoxy)carbonyl]amino}propanoic acid;MFCD00080284;AKOS015836460;AKOS015896022;Nalpha-Boc-O-(dibenzylphospho)-L-serine;AS-73696;CS-0179127;Boc-Ser(PO3Bzl2)-OH, >=96.0% (TLC);M06198;Boc-O-dibenZylphospho-L-serine (Boc-L-Ser(PO(OBZl)2)-OH);O-[Bis(benzyloxy)phosphoryl]-N-(tert-butoxycarbonyl)-L-serine

Chemical Property of Boc-Ser(PO3Bzl2)-OH

Chemical Property:

• Vapor Pressure: 1.39E-16mmHg at 25°C
• Refractive Index: 1.549
• Boiling Point: 626.9oC at 760 mmHg
• Flash Point: 333oC
• PSA: 130.20000
• Density: 1.273g/cm3
• LogP: 4.91350
• Storage Temp.: 2-8°C
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 13
• Exact Mass: 465.15525385
• Heavy Atom Count: 32
• Complexity: 612

Purity/Quality:

98%min ^*data from raw suppliers

Boc-Ser(PO3Bzl2)-OH ≥96.0% (TLC) ^*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(COP(=O)(OCC1=CC=CC=C1)OCC2=CC=CC=C2)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](COP(=O)(OCC1=CC=CC=C1)OCC2=CC=CC=C2)C(=O)O

Technology Process of Boc-Ser(PO3Bzl2)-OH

There total 8 articles about Boc-Ser(PO3Bzl2)-OH 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: 85.0%

(Nα-t-butoxycarbonyl)-O-(dibenzylphosphono)-L-serine p-nitrobenzyl ester (90236-61-6) → Nα-(t-butoxycarbonyl)-O-(dibenzylphosphono)-L-serine (90013-45-9)

Guidance literature:

With sodium dithionite; sodium carbonate; In water; acetonitrile; at 50 ℃; for 1h;

Reference yield:

Nα-t-butoxycarbonyl-L-serine p-nitrobenzyl ester (16938-11-7) → Nα-(t-butoxycarbonyl)-O-(dibenzylphosphono)-L-serine (90013-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / pyridine / tetrahydrofuran / 6 h / -40 - -35 °C

2: 85 percent / sodium dithionite, sodium carbonate / H₂O; acetonitrile / 1 h / 50 °C

With pyridine; sodium dithionite; sodium carbonate; In tetrahydrofuran; water; acetonitrile;

Reference yield:

dibenzyl phosphochloridate (538-37-4) → Nα-(t-butoxycarbonyl)-O-(dibenzylphosphono)-L-serine (90013-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / pyridine / tetrahydrofuran / 6 h / -40 - -35 °C

2: 85 percent / sodium dithionite, sodium carbonate / H₂O; acetonitrile / 1 h / 50 °C

With pyridine; sodium dithionite; sodium carbonate; In tetrahydrofuran; water; acetonitrile;

upstream raw materials:

(N^α-t-butoxycarbonyl)-O-(dibenzylphosphono)-L-serine p-nitrobenzyl ester

dibenzyl phosphochloridate

N^α-t-butoxycarbonyl-L-serine p-nitrobenzyl ester

(S)-N-(tert-butoxycarbonyl)serine

Downstream raw materials:

Nα-(t-butoxycarbonyl)-O-(benzyl)glutamyl-O-(dibenzylphosphono)serylleucine benzyl ester

(S)-2-[(S)-2-Amino-3-(bis-benzyloxy-phosphoryloxy)-propionylamino]-4-methyl-pentanoic acid benzyl ester

Boc-Ser(PO₃Bzl₂)-Leu-OBzl

Refernces

• 1、 Alewood, Paul F.,Perich, John W.,Johns, R. B.. "Preparation of Nα-(t-Butoxycarbonyl)-O-(dibenzylphosphono)-L-serine". . p. 429 - 433. Retrieved 2007/10/02.