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N-Cbz-D-Serine, also known as N-Benzyloxycarbonyl-D-serine, is a derivative of D-serine (S270975) with its amine group protected from electrophiles by a carboxybenzyl group. This protection is crucial in organic synthesis, as it allows for the selective modification of other functional groups without affecting the amine.

6081-61-4

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6081-61-4 Usage

Uses

Used in Pharmaceutical Industry:
N-Cbz-D-Serine is used as an intermediate in the synthesis of various pharmaceutical compounds. Its primary application is in the production of acetamido-methoxypropionamides, such as Desacetyl Desmethyl Lacosamide (D288325), which is a potent anticonvulsant. This makes N-Cbz-D-Serine a valuable component in the development of new treatments for epilepsy and other seizure disorders.

Check Digit Verification of cas no

The CAS Registry Mumber 6081-61-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,0,8 and 1 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 6081-61:
(6*6)+(5*0)+(4*8)+(3*1)+(2*6)+(1*1)=84
84 % 10 = 4
So 6081-61-4 is a valid CAS Registry Number.
InChI:InChI=1/C11H13NO5/c13-6-9(10(14)15)12-11(16)17-7-8-4-2-1-3-5-8/h1-5,9,13H,6-7H2,(H,12,16)(H,14,15)/t9-/m1/s1

6081-61-4 Well-known Company Product Price

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  • TCI America

  • (C2137)  N-Carbobenzoxy-D-serine  >98.0%(T)

  • 6081-61-4

  • 1g

  • 330.00CNY

  • Detail
  • TCI America

  • (C2137)  N-Carbobenzoxy-D-serine  >98.0%(T)

  • 6081-61-4

  • 5g

  • 990.00CNY

  • Detail
  • Alfa Aesar

  • (L08384)  N-Benzyloxycarbonyl-D-serine, 98+%   

  • 6081-61-4

  • 250mg

  • 221.0CNY

  • Detail
  • Alfa Aesar

  • (L08384)  N-Benzyloxycarbonyl-D-serine, 98+%   

  • 6081-61-4

  • 1g

  • 687.0CNY

  • Detail
  • Alfa Aesar

  • (L08384)  N-Benzyloxycarbonyl-D-serine, 98+%   

  • 6081-61-4

  • 5g

  • 1582.0CNY

  • Detail

6081-61-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name N-Cbz-D-Serine

1.2 Other means of identification

Product number -
Other names (2R)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6081-61-4 SDS

6081-61-4Relevant articles and documents

Switching Lysophosphatidylserine G Protein-Coupled Receptor Agonists to Antagonists by Acylation of the Hydrophilic Serine Amine

Sayama, Misa,Uwamizu, Akiharu,Ikubo, Masaya,Chen, Luying,Yan, Ge,Otani, Yuko,Inoue, Asuka,Aoki, Junken,Ohwada, Tomohiko

, p. 10059 - 10101 (2021/07/28)

Three human G protein-coupled receptors (GPCRs)—GPR34/LPS1, P2Y10/LPS2, and GPR174/LPS3—are activated specifically by lysophosphatidylserine (LysoPS), an endogenous hydrolysis product of a cell membrane component, phosphatidylserine (PS). LysoPS consists of-serine, glycerol, and fatty acid moieties connected by phosphodiester and ester linkages. We previously generated potent and selective GPCR agonists by modification of the three modules and the ester linkage. Here, we show that a novel modification of the hydrophilic serine moiety, that is, N-acylations of the serine amine, converted a GPR174 agonist to potent GPR174 antagonists. Structural exploration of the amide functionality provided access to a range of activities from agonist to partial agonist to antagonist. The present study would provide a new strategy for the development of lysophospholipid receptor antagonists.

Practical Cleavage of Acetals by Using an Odorless Thiol Immobilized on Silica

de Léséleuc, Mylène,Kukor, Andrew,Abbott, Shaun D.,Zacharie, Boulos

, p. 7389 - 7393 (2019/12/03)

A practical, efficient and general method was developed for the deprotection of a variety of aromatic and aliphatic acetals to their corresponding catechol or diol derivatives using thiol immobilized on silica gel. This is an application for the well-known commercial solid-supported thiol (SiliaMetS Thiol). The procedure is mild and amenable to scale-up. It does not require inert atmosphere and clean conversions were observed. This method is applicable to substituted 1,3-benzodioxole and aliphatic acetals with different functionalities. It offers the advantage of a general route with high yield, which can be undertaken at ambient temperature.

Toward aplyronine payloads for antibody-drug conjugates: Total synthesis of aplyronines A and D

An?i?ek, Nika,Williams, Simon,Housden, Michael P.,Paterson, Ian

supporting information, p. 1343 - 1350 (2018/03/06)

The aplyronines are a family of antimitotic marine macrolides that disrupt cytoskeletal dynamics by dual targeting of both actin and tubulin. Given their picomolar cytotoxicity profile and unprecedented mode of action, the aplyronines represent an excellent candidate as a novel payload for the development of next-generation antibody-drug conjugates (ADCs) for cancer chemotherapy. Enabled by an improved second-generation synthesis of the macrolactone core 5, we have achieved the first total synthesis of the most potent congener aplyronine D together with a highly stereocontrolled synthesis of aplyronine A. To facilitate step economy, an adventurous site-selective esterification of the C7 hydroxyl group was performed to install the N,N,O-trimethylserine pharmacophore to directly afford aplyronines A and D. Toward the assembly of ADCs incorporating an aplyronine warhead, the C29-ester derivative 4 featuring an Fmoc-amino substituted linker attached to the actin-binding tail region was also prepared by adapting this flexible endgame.

Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers

Wang, Shengyang,Sun, Jiansong,Zhang, Qingju,Cao, Xin,Zhao, Yachen,Tang, Gongli,Yu, Biao

supporting information, p. 2884 - 2888 (2018/02/16)

The proposed diastereoisomers (1 a–d) together with their C8′-epimers (1 e–h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereodivergent, and features a stereoselective aldol condensation to build the branched C9 sugar amino acid skeleton and a regio- and stereocontrolled gold(I)-catalyzed N-glycosylation to furnish the purine nucleoside. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3′ in amipurimycin should be of opposite configuration.

An efficient and facile synthesis of D-cycloserine substantially free from potential impurities

Awasthi, Arun Kumar,Kumar, Brijesh,Aga, Mushtaq A,Tripathi, Punit,Reddy, Cirandur Suresh,Kumar, Pramod

, p. 1248 - 1253 (2018/02/14)

An efficient and facile synthesis of D-cycloserine has been developed from D-serine with 61% overall yield employing protectiondeprotection strategy. Different parameters affecting the impurities content and yield of D-cycloserine have been studied. Mild reaction conditions provided the product with remarkable purity (>99%) and high stability.

Application of Methyl Bisphosphine-Ligated Palladium Complexes for Low Pressure N-11C-Acetylation of Peptides

Andersen, Thomas L.,Nordeman, Patrik,Christoffersen, Heidi F.,Audrain, Hélène,Antoni, Gunnar,Skrydstrup, Troels

supporting information, p. 4549 - 4553 (2017/04/13)

A mild and effective method is described for 11C-labeling of peptides selectively at the N-terminal nitrogen or at internal lysine positions. The presented method relies on the use of specific biphosphine palladium–methyl complexes and their high reactivity towards amino-carbonylation of amine groups in the presence [11C]carbon monoxide. The protocol facilitates the production of native N-11C-acetylated peptides, without any structural modifications and has been applied to a selection of bioactive peptides.

GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES

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Paragraph 000166, (2016/09/26)

Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme

GLUCOSYLCERAMIDE SYNTHASE INHIBITORS FOR THE TREATMENT OF DISEASES

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Paragraph 000219, (2015/04/15)

Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).

N-(1-HYDROXY-3-(PYRROLIDINYL)PROPAN-2-YL)PYRROLIDINE-3-CARBOXAMIDE DERIVATIVES AS GLUCOSYLCERAMIDE SYNTHASE INHIBITORS

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Paragraph 000201, (2015/05/19)

Described herein are compounds of Formula I, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and compounds I for use to treat or prevent diseases or conditions associated with the enzyme glucosylceramide synthase (GCS).

Lewis acid facilitated regioselective synthesis of τ-histidinoalanine

Wu, Ju,Ma, Bing,Wang, Yuehui,Zhang, Yue,Yan, Shenghu,Castle, Steven L.

, p. 3114 - 3116 (2014/05/20)

τ-Histidinoalanine, with an unusual cross-link between His and Ala, is the central component of theonellamides, a family of bioactive peptidic natural products. Previous syntheses of this residue were plagued with low regioselectivity in the alkylation step. Herein, we report two novel routes to τ-histidinoalanine, involving alkylation of Boc-His-OMe with a serine-derived β-lactone and β-bromoalanine, respectively, as the electrophiles. The use of Mg(OTf)2 as a catalyst was found to be essential to ensure high regioselectivity for the τ-isomer, presumably due to the formation of a six-membered ring chelation involving the π-nitrogen atom of histidine.

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