(2R,3R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-3,4-bis-triethylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran

Base Information

Chemical Name:(2R,3R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-3,4-bis-triethylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran
CAS No.:898552-26-6
Molecular Formula:C₃₈H₆₀O₆Si₂
Molecular Weight:669.062
Hs Code.:

Synonyms:(2R,3R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-3,4-bis-triethylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran

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Chemical Property of (2R,3R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-3,4-bis-triethylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran

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Technology Process of (2R,3R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-3,4-bis-triethylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran

There total 11 articles about (2R,3R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-3,4-bis-triethylsilanyloxy-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: 96.0%

: 898552-21-1
(2R,3S,4R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3,4-diol

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 898552-26-6
(2R,3R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-3,4-bis-triethylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane;
DOI:10.1016/j.tetlet.2006.04.018

Reference yield:

: 898552-15-3
(E)-(R)-1-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-penta-2,4-dien-1-ol

: 898552-26-6
(2R,3R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-3,4-bis-triethylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: Multi-step reaction with 3 steps

1.1: 88 percent / TBAF / tetrahydrofuran / 0.5 h

2.1: L-(+)-diethyl tartrate; Ti(O-iPr)4; t-BuOOH / 4 Angstroem molecular sieves / 1 h / -20 °C

2.2: 93 percent / PPTS / CH₂Cl₂ / 1 h

3.1: 96 percent / 2,6-lutidine / CH₂Cl₂

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; 4 A molecular sieve; In tetrahydrofuran; dichloromethane; 2.1: Sharpless epoxidation;
DOI:10.1016/j.tetlet.2006.04.018

Reference yield:

: (E)-1-[(2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-penta-2,4-dien-1-one

: 898552-26-6
(2R,3R,4R,4aS,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-3,4-bis-triethylsilanyloxy-2-vinyl-octahydro-pyrano[3,2-b]pyran

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaBH₄; CeCl₃*7H₂O / ethanol / 3 h / -78 - -55 °C

2.1: 88 percent / TBAF / tetrahydrofuran / 0.5 h

3.1: L-(+)-diethyl tartrate; Ti(O-iPr)4; t-BuOOH / 4 Angstroem molecular sieves / 1 h / -20 °C

3.2: 93 percent / PPTS / CH₂Cl₂ / 1 h

4.1: 96 percent / 2,6-lutidine / CH₂Cl₂

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium tetrahydroborate; cerium(III) chloride; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; 4 A molecular sieve; In tetrahydrofuran; ethanol; dichloromethane; 1.1: Luche reduction / 3.1: Sharpless epoxidation;
DOI:10.1016/j.tetlet.2006.04.018