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

Base Information

Chemical Name:(2S,3R,4aS,8aR)-3-((2R,3S)-2-Benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-vinyl-octahydro-pyrano[3,2-b]pyran
CAS No.:207805-84-3
Molecular Formula:C₂₃H₃₂O₅
Molecular Weight:388.504
Hs Code.:

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

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

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

There total 6 articles about (2S,3R,4aS,8aR)-3-((2R,3S)-2-Benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-vinyl-octahydro-pyrano[3,2-b]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: 71.0%

: 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

: 207805-84-3
(2S,3R,4aS,8aR)-3-((2R,3S)-2-Benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-vinyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; at -20 ℃;
DOI:10.1039/a801678j

Reference yield:

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

: 207805-84-3
(2S,3R,4aS,8aR)-3-((2R,3S)-2-Benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-vinyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: Multi-step reaction with 5 steps

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

2: Bu₄NF / tetrahydrofuran

3: TsOH*H₂O / toluene / 90 °C

4: 80 percent / tetrahydrofuran / -78 °C

5: 71 percent / Et₃SiH, BF₃*OEt₂ / acetonitrile / -20 °C

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

Reference yield:

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

: 207805-84-3
(2S,3R,4aS,8aR)-3-((2R,3S)-2-Benzyloxymethyl-tetrahydro-pyran-3-yloxy)-2-vinyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: Multi-step reaction with 5 steps

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

2: Bu₄NF / tetrahydrofuran

3: TsOH*H₂O / toluene / 90 °C

4: 80 percent / tetrahydrofuran / -78 °C

5: 71 percent / Et₃SiH, BF₃*OEt₂ / acetonitrile / -20 °C

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