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

Base Information

Chemical Name:(3aS,4R,6R,7aS)-6-Allyl-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one
CAS No.:874660-33-0
Molecular Formula:C₂₆H₃₂O₅Si
Molecular Weight:452.623
Hs Code.:

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

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Chemical Property of (3aS,4R,6R,7aS)-6-Allyl-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one

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Technology Process of (3aS,4R,6R,7aS)-6-Allyl-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one

There total 7 articles about (3aS,4R,6R,7aS)-6-Allyl-4-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one 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: 87.0%

: 874660-55-6
4-(tert-butyl-diphenyl-silanyloxymethyl)-6-ethoxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-one

: 762-72-1
allyl-trimethyl-silane

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

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

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -10 ℃; for 6h; optical yield given as %de;
DOI:10.1002/chem.200900776

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

With ruthenium trichloride; sodium periodate; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; 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

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

Guidance literature:: Multi-step reaction with 4 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

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