octyl 4-O-benzoyl-β-D-glucopyranoside

Base Information

• Chemical Name: octyl 4-O-benzoyl-β-D-glucopyranoside
• CAS No.: 1394172-54-3
• Molecular Formula: C₂₁H₃₂O₇
• Molecular Weight: 396.481
• Mol file: 1394172-54-3.mol

Synonyms:octyl 4-O-benzoyl-β-D-glucopyranoside

Chemical Property of octyl 4-O-benzoyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of octyl 4-O-benzoyl-β-D-glucopyranoside

There total 3 articles about octyl 4-O-benzoyl-β-D-glucopyranoside 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: 87.0%

benzoyl chloride (98-88-4) + n-octyl β-D-glucopyranoside (29836-26-8) → octyl 4-O-benzoyl-β-D-glucopyranoside (1394172-54-3)

Guidance literature:

With (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine; N-ethyl-N,N-diisopropylamine; Trimethylacetic acid; In chloroform; at -20 ℃; for 0.25h; Reagent/catalyst; Catalytic behavior;

DOI:10.1021/acs.orglett.7b01213

Reference yield: 25.0%

N-Cbz-L-Phe (1161-13-3) + benzoic acid anhydride (93-97-0) + n-octyl β-D-glucopyranoside (29836-26-8) → octyl 4-O-((S)-2-benzyloxycarbonylamino-3-phenylpropanoyl)-β-D-glucopyranoside (1194234-22-4) + octyl 4-O-benzoyl-β-D-glucopyranoside (1394172-54-3)

Guidance literature:

N-Cbz-L-Phe; benzoic acid anhydride; With 2,4,6-trimethyl-pyridine; In chloroform; at 20 ℃; for 1h; Inert atmosphere;

n-octyl β-D-glucopyranoside; With (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine; In chloroform; at -20 ℃; for 120h; regioselective reaction; Catalytic behavior; Inert atmosphere;

DOI:10.1021/jo301007x

Reference yield:

benzoyl chloride (98-88-4) + n-octyl β-D-glucopyranoside (29836-26-8) → octyl 4-O-benzoyl-β-D-glucopyranoside (1394172-54-3) + octyl 3-O-benzoyl-β-D-glucopyranoside

Guidance literature:

With (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine; N-ethyl-N,N-diisopropylamine; Trimethylacetic acid; In chloroform; at -20 ℃; for 0.25h; Catalytic behavior;

DOI:10.1021/acs.orglett.7b01213

upstream raw materials:

N-Cbz-L-Phe

benzoic acid anhydride

n-octyl β-D-glucopyranoside

benzoyl chloride

Refernces

• 1、 Yanagi, Masanori,Imayoshi, Ayumi,Ueda, Yoshihiro,Furuta, Takumi,Kawabata, Takeo. "Carboxylate Anions Accelerate Pyrrolidinopyridine (PPy)-Catalyzed Acylation: Catalytic Site-Selective Acylation of a Carbohydrate by in Situ Counteranion Exchange". . p. 3099 - 3102. Retrieved 2017.