(3R,4aS,8aR)-3-((2R,3S)-2-Benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-vinyl-octahydro-pyrano[3,2-b]pyran-2-ol

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Chemical Name:(3R,4aS,8aR)-3-((2R,3S)-2-Benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-vinyl-octahydro-pyrano[3,2-b]pyran-2-ol
CAS No.:207805-79-6
Molecular Formula:C₂₃H₃₂O₆
Molecular Weight:404.503
Hs Code.:

Synonyms:(3R,4aS,8aR)-3-((2R,3S)-2-Benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-vinyl-octahydro-pyrano[3,2-b]pyran-2-ol

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Chemical Property of (3R,4aS,8aR)-3-((2R,3S)-2-Benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-vinyl-octahydro-pyrano[3,2-b]pyran-2-ol

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Technology Process of (3R,4aS,8aR)-3-((2R,3S)-2-Benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-vinyl-octahydro-pyrano[3,2-b]pyran-2-ol

There total 5 articles about (3R,4aS,8aR)-3-((2R,3S)-2-Benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-vinyl-octahydro-pyrano[3,2-b]pyran-2-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: 80.0%

: 1826-67-1
vinyl magnesium bromide

: 207805-76-3
(3R,4aS,8aR)-3-((2R,3S)-2-Benzyloxymethyl-tetrahydro-pyran-3-yloxy)-hexahydro-pyrano[3,2-b]pyran-2-one

: 207805-79-6
(3R,4aS,8aR)-3-((2R,3S)-2-Benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-vinyl-octahydro-pyrano[3,2-b]pyran-2-ol

Guidance literature:: In tetrahydrofuran; at -78 ℃;
DOI:10.1039/a801678j

Reference yield:

: ((2R,3R)-2-Iodomethyl-tetrahydro-pyran-3-yloxy)-triisopropyl-silane

: 207805-79-6
(3R,4aS,8aR)-3-((2R,3S)-2-Benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-vinyl-octahydro-pyrano[3,2-b]pyran-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1: LDA, HMPA / tetrahydrofuran / -78 - 0 °C

2: Bu₄NF / tetrahydrofuran

3: TsOH*H₂O / toluene / 90 °C

4: 80 percent / tetrahydrofuran / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; toluene;
DOI:10.1039/a801678j

Reference yield:

: ((2R,3S)-2-Benzyloxymethyl-tetrahydro-pyran-3-yloxy)-acetic acid tert-butyl ester

: 207805-79-6
(3R,4aS,8aR)-3-((2R,3S)-2-Benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-vinyl-octahydro-pyrano[3,2-b]pyran-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1: LDA, HMPA / tetrahydrofuran / -78 - 0 °C

2: Bu₄NF / tetrahydrofuran

3: TsOH*H₂O / toluene / 90 °C

4: 80 percent / tetrahydrofuran / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; toluene;
DOI:10.1039/a801678j