10433-52-0

Basic information

• Product Name: O-BENZYL-D-SERINE
• Synonyms: D-SERINE BENZYL ETHER;D-SERINE(BZL)-OH;H-D-SER(BZL)-OH;O-BENZYL-D-SERINE;(R)-2-AMINO-3-BENZYLOXYPROPIONIC ACID;(R)-2-Amino-3-Benzyloxypropionic acid,O-Benzyl-D-serine;(R)-2-Amino-3-(benzyloxy)propanoic acid;O-(Phenylmethyl)-D-serine
• CAS NO: 10433-52-0
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.22
• EINECS: 233-916-6
• Mol File: 10433-52-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: ~227 °C (dec.)
• Boiling Point: 359.053 °C at 760 mmHg
• Flash Point: 170.949 °C
• Appearance: /
• Density: 1.217
• Vapor Pressure: 8.83E-06mmHg at 25°C
• Refractive Index: 1.56
• Storage Temp.: Store at 0-5°C
• PKA: 2.10±0.10(Predicted)
• BRN: 2649409
• CAS DataBase Reference: O-BENZYL-D-SERINE(CAS DataBase Reference)
• NIST Chemistry Reference: O-BENZYL-D-SERINE(10433-52-0)
• EPA Substance Registry System: O-BENZYL-D-SERINE(10433-52-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 10433-52-0(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

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.

InChI:InChI=1/C10H13NO3/c11-9(10(12)13)7-14-6-8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)/t9-/m1/s1

Upstream product

• 47173-80-8 N-Boc-D-serine(Bzl)-OH 
• 100-39-0 benzyl bromide 
• 5445-44-3 O-benzylserine 
• 84907-80-2 (3S,6R)-6-Benzyloxy-2,5-dimethoxy-3-(3,4-dimethoxybenzyl)-3-methyl-3,6-dihydropyrazine 
• 84907-79-9 (3R,6S)-3-Benzyloxymethyl-2,5-dimethoxy-6-isopropyl-3,6-dihydropyrazine 
• 3587-60-8 Benzyloxymethyl chloride 
• 1233494-98-8 (R)-O-Benzylserine hydrochloride 
• 20409-07-8 N-Formyl-O-benzyl-DL-serin 
• 84907-81-3 (2R)-3-benzyloxy-2-aminopropanoic acid methyl ester 

Downstream Products

• 1448013-34-0 2-N-acetyl-6-O-allyl-3,4-di-O-benzyl-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-O-levulinoyl-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate 
• 1448013-23-7 2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate 
• 1448013-36-2 2-N-acetyl-3,4-di-O-benzyl-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate 
• 1448013-24-8 2-N-acetyl-3,4-di-O-benzyl-6-O-prop-1-en-α-D-glucosaminopyranosyl-(1→3)-2-N-acetyl-4-O-benzyl-6-((N,N,-diisopropylamino)-2-cyanoethylphosphite)-α-D-glucosaminopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate 
• 1448013-31-7 2-azido-4-O-benzyl-2-deoxy-6-O-levulinoyl-3-O-(2-naphthalenylmethyl)-α-D-glucopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate 
• 1448013-32-8 2-azido-4-O-benzyl-2-deoxy-6-O-levulinoyl-α-D-glucopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate 
• 1448013-33-9 6-O-allyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1→3)-2-azido-4-O-benzyl-2-deoxy-6-O-levulinoyl-α-D-glucopyranosyl-(1→2)-benzyl (2R)-3-benzyloxypropanoate 
• 226699-20-3 (R)-N-benzyloxycarbonyl O-benzyl serinamide 
• 446253-69-6 (2R)-2-azido-N-benzyl-3-benzyloxypropionamide 

Relevant articles and documents

Amine-boranes: Effective reducing agents for the deracemisation of DL-amino acids using L-amino acid oxidase from Proteus myxofaciens

The deracemisation of DL-α-amino acids using L-amino acid oxidase from Proteus myxofaciens and amine-boranes as chemical reducing agents has been investigated. Amine-boranes were found to be of particular interest in terms of reactivity and chemoselectivity compared to sodium borohydride and cyanoborohydride. Starting from the racemate, a range of D-amino acids were obtained in yields of up to 90% and e.e. >99%.

Cinnamic acid derivative with aldose reductase inhibitory activity as well as preparation method and application thereof

The invention discloses a cinnamic acid derivative with aldose reductase inhibitory activity, a preparation method thereof and an application of the cinnamic acid derivative in preparation of a medicine used for treating diabetic complications and diseases caused by oxidative stress. The structure of the compound is shown in a formula I. The preparation method comprises the following steps: firstly reacting substituted benzaldehyde with substituted acetic acid or acid anhydride thereof to obtain substituted cinnamic acid, then reacting with a diamine compound protected by N-tertiary butoxy acyl to obtain substituted cinnamoyl diamide protected by N-tertiary butoxy acyl; and carrying out tertiary butoxy acyl deprotection on the substituted cinnamoyl diamide protected by N-tertiary butoxy acyl, and then reacting with natural or non-natural N-acyl alpha-amino acid, so that the cinnamic acid derivative is obtained. The cinnamic acid derivative compound disclosed by the invention has excellent inhibitory activity on aldose reductase and excellent antioxidant activity and can be applied to preparation of a medicine used for treating the diabetic complications, especially diabetic retinopathy, senile dementia due to diabetes and nerve ending disturbance, as well as diseases caused by the oxidative stress.

Optical resolution of O-benzyl-N-formyl-(R)-(S)-serine

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