Boc-D-Ser-OBzl

Base Information

• Chemical Name: Boc-D-Ser-OBzl
• CAS No.: 141527-78-8
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.335
• European Community (EC) Number: 888-978-2
• DSSTox Substance ID: DTXSID30513810
• Wikidata: Q72510492
• Mol file: 141527-78-8.mol

Synonyms:Boc-D-Ser-OBzl;141527-78-8;Boc-D-Ser-O-Bzl;Boc-D-serine benzyl ester;Benzyl (tert-butoxycarbonyl)-D-serinate;benzyl (2R)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate;MFCD00080265;D-Serine, N-[(1,1-dimethylethoxy)carbonyl]-, phenylmethyl ester;N-Boc-D-serine benzyl ester;(R)-Benzyl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate;Benzyl N-(tert-butoxycarbonyl)-D-serinate;Boc-(D)-serine benzyl ester;SCHEMBL7172323;DTXSID30513810;BQADRZHPZVQGCW-GFCCVEGCSA-N;AKOS016842937;AM82218;CS-W009973;HY-W009257;AS-71523;Boc-D-Ser-O-Bzl, >=95.0% (HPLC);F10633;A847912;J-300230;Q-101714;N-[(tert-Butoxy)carbonyl]-D-serine phenylmethyl ester;(R)-benzyl 2-(tert-butoxycarbonylamino)-3-hydroxypropanoate;benzyl (2R)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxypropanoate

Chemical Property of Boc-D-Ser-OBzl

Chemical Property:

• Vapor Pressure: 3.25E-09mmHg at 25°C
• Melting Point: 66-70℃
• Refractive Index: 1.523
• Boiling Point: 458.846 °C at 760 mmHg
• PKA: 10.67±0.46(Predicted)
• Flash Point: 231.302 °C
• PSA: 84.86000
• Density: 1.174 g/cm³
• LogP: 2.00630
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 295.14197277
• Heavy Atom Count: 21
• Complexity: 345

Purity/Quality:

98% ^*data from raw suppliers

Boc-D-serine benzyl ester ^*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)C(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CO)C(=O)OCC1=CC=CC=C1
• Uses: Boc-D-Ser-O-Bzl is a serine derivative with N-Boc & COOH-benzyl ester protection. Also, it is a reagent used in the synthesis of anti-fungal dilactones, UK-2A and UK-3A.

Technology Process of Boc-D-Ser-OBzl

There total 4 articles about Boc-D-Ser-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: 65.0%

(R)-N-tert-butoxycarbonyl serine (3262-72-4,3850-40-6,6368-20-3,90582-28-8,84311-18-2) + benzyl bromide (100-39-0) → (R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate (59524-02-6,145612-59-5,141527-78-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1016/j.cclet.2012.03.032

Reference yield:

C8H14NO5(1-)*K(1+) + benzyl bromide (100-39-0) → (R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate (59524-02-6,145612-59-5,141527-78-8)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1016/j.bmc.2014.07.023

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate (59524-02-6,145612-59-5,141527-78-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate; sodium carbonate / water

2: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 24 h / 20 °C

With sodium hydride; sodium hydrogencarbonate; sodium carbonate; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1016/j.cclet.2012.03.032

upstream raw materials:

di-tert-butyl dicarbonate

D-serine benzyl ester

(R)-N-tert-butoxycarbonyl serine

benzyl bromide

Downstream raw materials:

(R)-2-tert-butoxycarbonylamino-3-phenylsulfanylpropionic acid methyl ester

benzyl (4R)-3-(tert-butyloxycarbonyl)-2,2-dioxo-1,2,3-oxathiazolidine-4-carboxylate

D-serine benzyl ester hydrochloride

(2S,6R)-3-Oxo-6-<(phenylmethoxy)carbonyl>-2-piperazineacetic acid methyl ester

Refernces

• 1、 Qi, Xian Liang,Yang, Er Qun,Zhang, Jun Tao,Wang, Tao,Cao, Xiao Ping. "A facile synthesis of the spiroindoline-based growth hormone secretagogue, MK-677". scheme or table. p. 661 - 664. Retrieved 2012/07/03.