CID 6950863

Base Information

• Chemical Name: CID 6950863
• CAS No.: 10433-52-0
• Molecular Formula: C10H13NO3
• Molecular Weight: 195.218
• Hs Code.: 2922500090
• Mol file: 10433-52-0.mol

Synonyms:BDBM36047

Chemical Property of CID 6950863

Chemical Property:

• Vapor Pressure: 8.83E-06mmHg at 25°C
• Melting Point: ~227°C (dec.)
• Refractive Index: 1.56
• Boiling Point: 359.053 °C at 760 mmHg
• PKA: 2.10±0.10(Predicted)
• Flash Point: 170.949 °C
• Density: 1.218 g/cm³
• Storage Temp.: Store at 0-5°C
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 195.08954328
• Heavy Atom Count: 14
• Complexity: 173

Purity/Quality:

99%, ^*data from raw suppliers

O-Benzyl-D-serine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COCC(C(=O)[O-])[NH3+]
• Isomeric SMILES: C1=CC=C(C=C1)COC[C@H](C(=O)[O-])[NH3+]
• Uses: O-Benzyl-D-serine has been shown to have been efficiently converted from D-5-monosubstitued hydatoin by E.coli thus revealing three co-expressed genes encoding hydantoin racemase, D-hydantoinase and N-carbamoyl-D-amino acid amidohydrolase.

Technology Process of CID 6950863

There total 12 articles about CID 6950863 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: 32.0%

N-Boc-D-serine(Bzl)-OH (47173-80-8) → O-benzyl-D-serine (10433-52-0,32520-12-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane;

DOI:10.1021/acschemneuro.7b00117

Reference yield:

O-benzylserine (5445-44-3,32520-12-0) → O-Benzyl-L-serine (4726-96-9,32520-12-0) + O-benzyl-D-serine (10433-52-0,32520-12-0)

Guidance literature:

With borane-ammonia complex; oxygen; ammonium formate; L-amino acid oxidase; In water; for 5h; pH=6.7;

DOI:10.1016/S0040-4039(01)02233-X

Reference yield:

benzyl bromide (100-39-0) → O-benzyl-D-serine (10433-52-0,32520-12-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0 - 20 °C

1.2: 0 - 20 °C

2.1: hydrogenchloride / 1,4-dioxane

With hydrogenchloride; sodium hydride; In 1,4-dioxane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/acschemneuro.7b00117

upstream raw materials:

(R)-O-Benzylserine hydrochloride

O-benzylserine

Benzyloxymethyl chloride

(2R)-3-benzyloxy-2-aminopropanoic acid methyl ester

Downstream raw materials:

(R)-3-Benzyloxy-2-(2-tert-butoxycarbonylamino-2-methyl-propionylamino)-propionic Acid

(2R)-3-benzyloxy-2-aminopropanoic acid methyl ester

C₂₇H₃₂ClNO₆

1-(benzyloxymethyl)-4-(2-chloroethyl)-2-(4-methoxybenzyl)-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione

Refernces

• 1、 Maolanon, Alex R.,Risgaard, Rune,Wang, Shuang-Yan,Snoep, Yoran,Papangelis, Athanasios,Yi, Feng,Holley, David,Barslund, Anne F.,Svenstrup, Niels,Hansen, Kasper B.,Clausen, Rasmus P.. "Subtype-Specific Agonists for NMDA Receptor Glycine Binding Sites". . p. 1681 - 1687. Retrieved 2017.
• 2、 Nozulak, Joachim,Schoellkopf, Ulrich. "Asymmetric Syntheses via Heterocyclic Intermediates; XIV. Enantioselective Synthesis of (R)-Serine using L-Valine or O,O-Dimethyl-α-methyldopa as Chiral Auxiliary Reagents". . p. 866 - 868. Retrieved 2007/10/02.