(S)-((3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl)(4-methoxyphenyl)methanol

Base Information

Chemical Name:(S)-((3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl)(4-methoxyphenyl)methanol
CAS No.:889662-75-3
Molecular Formula:C₂₂H₂₆O₆
Molecular Weight:386.445
Hs Code.:

Synonyms:(S)-((3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl)(4-methoxyphenyl)methanol

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Chemical Property of (S)-((3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl)(4-methoxyphenyl)methanol

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Technology Process of (S)-((3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl)(4-methoxyphenyl)methanol

There total 1 articles about (S)-((3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl)(4-methoxyphenyl)methanol 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: 12.0%

: 104-92-7
1-bromo-4-methoxy-benzene

: 23558-05-6
3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose

: (R)-((3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl)(4-methoxyphenyl)methanol

: 889662-75-3
(S)-((3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl)(4-methoxyphenyl)methanol

Guidance literature:: 1-bromo-4-methoxy-benzene; With magnesium; In tetrahydrofuran; for 1h; Heating;

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1021/jo052418r

Reference yield: 77.0%

: 889662-75-3
(S)-((3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl)(4-methoxyphenyl)methanol

: 762-72-1
allyl-trimethyl-silane

: 889662-81-1
(3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-5-((R)-1-(4-methoxyphenyl)but-3-enyl)-2,2-dimethyl-6-phenoxyfuro[3,2-d][1,3]dioxol

Guidance literature:: With zirconium(IV) chloride; In acetonitrile; at 20 ℃; for 0.833333h;
DOI:10.1021/jo052418r

Reference yield:

: 889662-75-3
(S)-((3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxol-5-yl)(4-methoxyphenyl)methanol

: (3aR,3bS,7S,7aR,8aR)-7-(4-Methoxy-phenyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[3,2-b]pyran-5-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 77 percent / ZrCl₄ / acetonitrile / 0.83 h / 20 °C

2.1: ozone / CH₂Cl₂ / -78 °C

2.2: Me₂S / CH₂Cl₂ / 1 h / 25 °C

3.1: 93 percent / NaClO₂; aq. H₂O₂ / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

4.1: 92 percent / H₂ / Pd-C / methanol / 12 h / 20 °C

With sodium chlorite; hydrogen; dihydrogen peroxide; zirconium(IV) chloride; ozone; palladium on activated charcoal; In methanol; dichloromethane; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo052418r