(2R,3R,4aR,8aS)-2-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-ylmethyl)-2-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

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Chemical Name:(2R,3R,4aR,8aS)-2-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-ylmethyl)-2-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol
CAS No.:242808-76-0
Molecular Formula:C₂₂H₃₂O₆
Molecular Weight:392.492
Hs Code.:

Synonyms:(2R,3R,4aR,8aS)-2-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-ylmethyl)-2-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

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Chemical Property of (2R,3R,4aR,8aS)-2-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-ylmethyl)-2-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

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Technology Process of (2R,3R,4aR,8aS)-2-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-ylmethyl)-2-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

There total 15 articles about (2R,3R,4aR,8aS)-2-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-ylmethyl)-2-methoxy-octahydro-pyrano[3,2-b]pyran-3-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: 40.0%

: 245053-90-1
(2R,3S)-2-[4-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-3-ethanesulfinyl-3-ethylsulfanyl-2-hydroxy-butyl]-tetrahydro-pyran-3-ol

: 149-73-5
trimethyl orthoformate

: 242808-76-0
(2R,3R,4aR,8aS)-2-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-ylmethyl)-2-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

: 242808-78-2
(2R,3S,4aR,8aS)-2-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-ylmethyl)-2-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 20 - 25 ℃;
DOI:10.1055/s-1999-2784

Reference yield:

: (S)-2-Allyl-tetrahydro-pyran-3-ol

: 242808-76-0
(2R,3R,4aR,8aS)-2-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-ylmethyl)-2-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂CL₂, -78 deg C, 2.) CH₂Cl₂, -78 to 0 deg C

2: 1.) LiAlH₄, 2.) lipase Amano P, vinyl acetate / 1.) Et₂O, THF, -78 deg C, 2.) 21-24 deg C

3: imidazole / dimethylformamide / 1.33 h / 22 °C

4: NMO, OsO₄, H₂O / dioxane / 4 h / 19 - 22 °C

5: NaIO₄, H₂O / dioxane / 1.5 h / 19 - 22 °C

6: LDA / tetrahydrofuran / 1.) -78 deg C, 20 min, 2.) -78 deg C, 20 min

7: TBAF / tetrahydrofuran / 25 °C

8: 40 percent / TsOH*H₂O / methanol / 20 - 25 °C

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; vinyl acetate; N-methyl-2-indolinone; oxalyl dichloride; lipase Amano P; tetrabutyl ammonium fluoride; water; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide;
DOI:10.1055/s-1999-2784

Reference yield:

: 125877-91-0
((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-yl)-acetaldehyde

: 242808-76-0
(2R,3R,4aR,8aS)-2-((2S,3R)-3-Benzyloxy-tetrahydro-pyran-2-ylmethyl)-2-methoxy-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1: ZnI₂ / CH₂Cl₂ / 2 h / 20 °C

2: m-CPBA / CH₂Cl₂ / 1 h / -78 °C

3: LDA / tetrahydrofuran / 1.) -78 deg C, 20 min, 2.) -78 deg C, 20 min

4: TBAF / tetrahydrofuran / 25 °C

5: 40 percent / TsOH*H₂O / methanol / 20 - 25 °C

With tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; zinc(II) iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1055/s-1999-2784