(2R,3S,4S,6R)-6-Allyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol

Base Information

Chemical Name:(2R,3S,4S,6R)-6-Allyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol
CAS No.:874660-56-7
Molecular Formula:C₂₅H₃₄O₄Si
Molecular Weight:426.628
Hs Code.:

Synonyms:(2R,3S,4S,6R)-6-Allyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol

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Chemical Property of (2R,3S,4S,6R)-6-Allyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol

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Technology Process of (2R,3S,4S,6R)-6-Allyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol

There total 8 articles about (2R,3S,4S,6R)-6-Allyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-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: 76.0%

: 874660-33-0
(3aS,4R,6R,7aS)-6-Allyl-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one

: 874660-56-7
(2R,3S,4S,6R)-6-Allyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol

Guidance literature:: With potassium carbonate; In methanol; for 0.5h;
DOI:10.1021/ol0526625

Reference yield:

: 874660-54-5
tert-butyl-(6-ethoxy-5,6-dihydro-2H-pyran-2-ylmethoxy)-diphenyl-silane

: 874660-56-7
(2R,3S,4S,6R)-6-Allyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol

Guidance literature:: Multi-step reaction with 4 steps

1: 75 percent / sodium periodate; RuCl₃*7H₂O / H₂O; ethyl acetate; acetonitrile / 0.02 h / 0 °C

2: 90 percent / tetrahydrofuran / 2.5 h / Heating

3: trimethylsilyl triflate / acetonitrile / -10 °C

4: 76 percent / potassium carbonate / methanol / 0.5 h

With ruthenium trichloride; sodium periodate; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; In tetrahydrofuran; methanol; water; ethyl acetate; acetonitrile; 2: Hosomi-Sakurai reaction;
DOI:10.1021/ol0526625

Reference yield:

: 874660-28-3
tert-butyl-[2-(1-ethoxy-but-3-enyloxy)-but-3-enyloxy]-diphenyl-silane

: 874660-56-7
(2R,3S,4S,6R)-6-Allyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / 2.5 h / 40 °C

1.2: 93 percent / CH₂Cl₂; dimethylsulfoxide / 20 °C

2.1: 75 percent / sodium periodate; RuCl₃*7H₂O / H₂O; ethyl acetate; acetonitrile / 0.02 h / 0 °C

3.1: 90 percent / tetrahydrofuran / 2.5 h / Heating

4.1: trimethylsilyl triflate / acetonitrile / -10 °C

5.1: 76 percent / potassium carbonate / methanol / 0.5 h

With ruthenium trichloride; sodium periodate; Grubbs catalyst first generation; trimethylsilyl trifluoromethanesulfonate; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetonitrile; 3.1: Hosomi-Sakurai reaction;
DOI:10.1021/ol0526625