(2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-phenethoxytetrahydro-2H-pyran

Base Information

Chemical Name:(2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-phenethoxytetrahydro-2H-pyran
CAS No.:1093681-14-1
Molecular Formula:C₄₂H₄₄O₆
Molecular Weight:644.808
Hs Code.:

Synonyms:(2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-phenethoxytetrahydro-2H-pyran

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Chemical Property of (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-phenethoxytetrahydro-2H-pyran

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Technology Process of (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-phenethoxytetrahydro-2H-pyran

There total 6 articles about (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-phenethoxytetrahydro-2H-pyran 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: 78.0%

: C₄₄H₄₆O₈

: 1093681-14-1
(2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-phenethoxytetrahydro-2H-pyran

Guidance literature:: C₄₄H₄₆O₈; With triethylsilane; In dichloromethane; at -78 ℃; for 0.166667h; Inert atmosphere;

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 0.5h; diastereoselective reaction; Inert atmosphere;
DOI:10.1021/acs.orglett.6b03683

Reference yield: 9.0%

: 4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9
2,3,4,6-Tetra-O-benzyl-D-glucopyranose

: 60-12-8
2-phenylethanol

: 1093681-07-2
2-phenylethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

: 1093681-14-1
(2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-phenethoxytetrahydro-2H-pyran

: 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside

Guidance literature:: With bismuth(lll) trifluoromethanesulfonate; calcium sulfate; In dichloromethane; for 0.25h; optical yield given as %de; Reflux;
DOI:10.3987/COM-08-S(F)41

Reference yield:

: 103-82-2
phenylacetic acid

: 1093681-14-1
(2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-phenethoxytetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 3 steps

1.1: N-ethyl-N,N-diisopropylamine; 2,2-dimethylpropanoic anhydride; (R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole / chloroform / 24 h / 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane / 0.83 h / -78 °C / Inert atmosphere

2.2: 4 h / -78 °C / Inert atmosphere

2.3: 0.5 h / 0 °C / Inert atmosphere

3.1: triethylsilane / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

3.2: 0.5 h / -78 °C / Inert atmosphere

With (R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; triethylsilane; 2,2-dimethylpropanoic anhydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In dichloromethane; chloroform;
DOI:10.1021/acs.orglett.6b03683