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

Base Information

Chemical Name:(2R,3S,4R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3,4-diol
CAS No.:898552-21-1
Molecular Formula:C₂₆H₃₂O₆
Molecular Weight:440.536
Hs Code.:

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

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

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

There total 11 articles about (2R,3S,4R,4aR,6S,7R,8aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-vinyl-octahydro-pyrano[3,2-b]pyran-3,4-diol 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: 93.0%

: 898552-17-5
(2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-((E)-(R)-1-hydroxy-penta-2,4-dienyl)-2-methyl-tetrahydro-pyran-3-ol

: 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

Guidance literature:: (2S,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-((E)-(R)-1-hydroxy-penta-2,4-dienyl)-2-methyl-tetrahydro-pyran-3-ol; With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; at -20 ℃; for 1h;

With pyridinium p-toluenesulfonate; In dichloromethane; for 1h;
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

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

Guidance literature:: Multi-step reaction with 2 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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; tetrabutyl ammonium fluoride; 4 A molecular sieve; In tetrahydrofuran; 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

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

Guidance literature:: Multi-step reaction with 3 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

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