(2R,4aR,6S,7R,8S,8aR)-7,8-Bis-allyloxy-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

Chemical Name:(2R,4aR,6S,7R,8S,8aR)-7,8-Bis-allyloxy-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
CAS No.:345342-71-4
Molecular Formula:C₂₆H₃₀O₆
Molecular Weight:438.521
Hs Code.:

Synonyms:(2R,4aR,6S,7R,8S,8aR)-7,8-Bis-allyloxy-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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Chemical Property of (2R,4aR,6S,7R,8S,8aR)-7,8-Bis-allyloxy-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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Technology Process of (2R,4aR,6S,7R,8S,8aR)-7,8-Bis-allyloxy-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 1 articles about (2R,4aR,6S,7R,8S,8aR)-7,8-Bis-allyloxy-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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%

: 79549-73-8
benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside

: 106-95-6
allyl bromide

: 345342-71-4
(2R,4aR,6S,7R,8S,8aR)-7,8-Bis-allyloxy-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(01)00355-0

Reference yield: 93.0%

: 345342-71-4
(2R,4aR,6S,7R,8S,8aR)-7,8-Bis-allyloxy-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 345342-61-2
(2R,3R,4S,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-ol

Guidance literature:: With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; for 0.166667h;
DOI:10.1021/ol010089t

Reference yield:

: 345342-71-4
(2R,4aR,6S,7R,8S,8aR)-7,8-Bis-allyloxy-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 345342-54-3
Benzoic acid (2S,3R,4R,5S,6R)-2-benzyloxy-6-benzyloxymethyl-4,5-dihydroxy-5-methyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 93 percent / sodium cyanoborohydride; HCl; 3 Angstroem molecular sieve / tetrahydrofuran; diethyl ether / 0.17 h

2.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

3.1: 66 percent / diethyl ether / 0.5 h / -78 °C

4.1: 100 percent / p-toluenesulfonic acid monohydrate / Pd/C / methanol; H₂O / 12 h / 70 °C

5.1: dibuthyltin oxide / benzene; methanol / 12 h / 70 °C

5.2: 100 percent / Et₃N / dioxane / 0.5 h / 20 °C

With hydrogenchloride; 3 A molecular sieve; di(n-butyl)tin oxide; sodium cyanoborohydride; Dess-Martin periodane; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; benzene;
DOI:10.1021/ol010089t