Boc-Hyp(Bzl)-OH

Base Information

• Chemical Name: Boc-Hyp(Bzl)-OH
• CAS No.: 54631-81-1
• Molecular Formula: C17H23NO5
• Molecular Weight: 335.4
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID20474507
• Nikkaji Number: J1.085.325G
• Wikidata: Q72448647
• Mol file: 54631-81-1.mol

Synonyms:Boc-Hyp(Bzl)-OH;54631-81-1;(2S,4R)-4-(Benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid;Boc-O-benzyl-trans-4-hydroxy-L-proline;(2S,4R)-1-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenylmethoxypyrrolidine-2-carboxylic acid;Trans-4-(Benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid;1240530-73-7;MFCD00037325;Boc-Hyp(bzl);SCHEMBL376159;DTXSID20474507;DGIGGVANZFKXLS-KGLIPLIRSA-N;AKOS015924089;AKOS015998709;AM81836;CS-W009892;DS-15957;N-t-butoxycarbonyl-4(R)-benzyloxyproline;N-t-butoxycarbonyl-4(R)- benzyloxyproline;Boc-Hyp(Bzl)-OH, >=98.0% (HPLC);trans-N-t-butoxycarbonyl-4-benzyloxy-L-proline;A830275;(4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)-L-proline;Boc-Hyp(Bzl)-OH inverted exclamation mark currencyDCHA;N-ALPHA-T-BUTYLOXYCARBONYL-L-4-O-BENZYL-HYDROXYPROLINE;(2S,4R)-4-Benzyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester;(2S,4R)-4-(benzyloxy)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

Chemical Property of Boc-Hyp(Bzl)-OH

Chemical Property:

• Appearance/Colour: white - off-white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: ~70 °C
• Refractive Index: 1.557
• Boiling Point: 461.342 °C at 760 mmHg
• PKA: 3.75±0.40(Predicted)
• Flash Point: 232.812 °C
• PSA: 76.07000
• Density: 1.22 g/cm³
• LogP: 2.60370
• Storage Temp.: Store at 0°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 321.15762283
• Heavy Atom Count: 23
• Complexity: 425

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-O-benzyl-L-trans-4-hydroxyproline dicyclohexylammonium salt 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CC(CC1C(=O)O)OCC2=CC=CC=C2
• Isomeric SMILES: CC(C)(C)OC(=O)N1C[C@@H](C[C@H]1C(=O)O)OCC2=CC=CC=C2
• Uses: Boc-Hyp(Bzl)-OH, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.

Technology Process of Boc-Hyp(Bzl)-OH

There total 20 articles about Boc-Hyp(Bzl)-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: 100.0%

benzyl bromide (100-39-0) + (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → (2S,4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (40350-83-2,54631-82-2,54631-81-1)

Guidance literature:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid; With sodium hydride; In tetrahydrofuran; dimethyl sulfoxide; mineral oil; at -20 - 0 ℃; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; dimethyl sulfoxide; mineral oil; at -20 - 25 ℃; for 6h; chemoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201402429

Reference yield: 97.0%

1-(tert-butyl) 2-methyl (2S,4R)-4-(benzyloxy)pyrrolidine-1,2-dicarboxylate (136024-60-7) → (2S,4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (40350-83-2,54631-82-2,54631-81-1)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; at 20 ℃; for 3h;

Reference yield: 94.0%

(2S,4S)-1-tert-butyl 2-methyl 4-(benzyloxy)pyrrolidine-1,2-dicarboxylate (262843-21-0) → (2S,4S)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (40350-83-2,54631-81-1,54631-82-2)

Guidance literature:

With lithium hydroxide; water; In tetrahydrofuran; at 20 ℃; for 48h;

upstream raw materials:

(2S,4S)-1-tert-butyl 2-methyl 4-(benzyloxy)pyrrolidine-1,2-dicarboxylate

(2S,4S)-2-benzyl 1-tert-butyl 4-(benzyloxy)pyrrolidine-1,2-dicarboxylate

benzyl bromide

N-tert-butoxycarbonyl-L-cis-4-hydroxyproline

Downstream raw materials:

2-[(N-tert-butoxycarbonyl-4(R)-benzyloxy)-L-prolyl]1,2,3,4-tetrahydro-9H-pyrido[3,4-b ]indole

(2S,4R)-tert-butyl 4-(benzyloxy)-2-(3-bromo-2-(3,5-difluorophenylcarbamoyl)-1H-pyrrol-1-ylcarbamoyl)pyrrolidine-1-carboxylate

ethyl 2-[4-[(4R)-benzyloxy-1-tert-butoxycarbonyl-(2S)-pyrrolidinylcarbonyl]-1-piperazinyl]-2-methylpropionate

Refernces

• 1、 -. "HETEROCYCLIC COMPOUNDS FOR USE IN THE TREATMENT OF CANCER". Paragraph 65; 66. . Retrieved 2021/02/19.
• 2、 Khong, San N.,Xie, Changmin,Wang, Xinyi,Tan, Hao,Kwon, Ohyun. "Chiral aminophosphines derived from hydroxyproline and their application in allene–imine [4 + 2] annulation". . p. 389 - 396. Retrieved 2019/04/08.