(2R,3R,4R,4aR,8aS)-3-(benzyloxy)-2-(phenoxymethyl)octahydropyrano[3,2-b]pyran-4-ol

Base Information

Chemical Name:(2R,3R,4R,4aR,8aS)-3-(benzyloxy)-2-(phenoxymethyl)octahydropyrano[3,2-b]pyran-4-ol
CAS No.:320576-38-3
Molecular Formula:C₂₃H₂₈O₅
Molecular Weight:384.472
Hs Code.:

Synonyms:(2R,3R,4R,4aR,8aS)-3-(benzyloxy)-2-(phenoxymethyl)octahydropyrano[3,2-b]pyran-4-ol

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Chemical Property of (2R,3R,4R,4aR,8aS)-3-(benzyloxy)-2-(phenoxymethyl)octahydropyrano[3,2-b]pyran-4-ol

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Technology Process of (2R,3R,4R,4aR,8aS)-3-(benzyloxy)-2-(phenoxymethyl)octahydropyrano[3,2-b]pyran-4-ol

There total 12 articles about (2R,3R,4R,4aR,8aS)-3-(benzyloxy)-2-(phenoxymethyl)octahydropyrano[3,2-b]pyran-4-ol 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: 72.0%

: 797010-98-1
(2R,3R,4R,4aR,8aS)-3,4-Bis-benzyloxy-2-benzyloxymethyl-octahydro-pyrano[3,2-b]pyran

: 320576-38-3
(2R,3R,4R,4aR,8aS)-3-(benzyloxy)-2-(phenoxymethyl)octahydropyrano[3,2-b]pyran-4-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; for 72h; Heating;
DOI:10.1016/j.tetlet.2004.09.030

Reference yield: 54.0%

: 320576-37-2
(5R,7S,8S,9S,10R)-8,9-bis(benzyloxy)-7-[(benzyloxy)methyl]-1,6-dioxaspiro[4,5]decan-10-yl methanesulfonate

: 320576-38-3
(2R,3R,4R,4aR,8aS)-3-(benzyloxy)-2-(phenoxymethyl)octahydropyrano[3,2-b]pyran-4-ol

: 320576-39-4
2,6-anhydro-1,3,4-tri-O-benzyl-7,8,9-trideoxy-D-glycero-D-gulo-nonitol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at 42 ℃; for 76h;
DOI:10.1021/jo005593a

Reference yield:

: 157794-06-4
2,6-anhydro-1,3,4-tri-O-benzyl-5-O-[tert-butyl(dimethyl)silyl]-7,8,9-trideoxy-D-glycerol-L-gulo-non-8-enitol

: 320576-38-3
(2R,3R,4R,4aR,8aS)-3-(benzyloxy)-2-(phenoxymethyl)octahydropyrano[3,2-b]pyran-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: BH₃*THF / tetrahydrofuran / 2 h / 0 °C

1.2: 83 percent / aq. H₂O₂; aq. NaOH / 0.5 h / 20 °C

2.1: 41 percent / DIB; I₂ / cyclohexane / 5 h / 20 °C

3.1: 95 percent / TBAF / tetrahydrofuran / 20 °C

4.1: 80 percent / pyridine / 5 h / 20 °C

5.1: 54 percent / DIBALH / CH₂Cl₂ / 76 h / 42 °C

With pyridine; borane-THF; 4,4'-diiodobiphenyl; tetrabutyl ammonium fluoride; iodine; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; cyclohexane;
DOI:10.1021/jo005593a