(1S,3aS,4S,6aR)-1-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furo[3,4-c]furan-3a-ol

Base Information

Chemical Name:(1S,3aS,4S,6aR)-1-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furo[3,4-c]furan-3a-ol
CAS No.:195141-59-4
Molecular Formula:C₃₀H₃₄O₆Si
Molecular Weight:518.682
Hs Code.:

Synonyms:(1S,3aS,4S,6aR)-1-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furo[3,4-c]furan-3a-ol

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Chemical Property of (1S,3aS,4S,6aR)-1-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furo[3,4-c]furan-3a-ol

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Technology Process of (1S,3aS,4S,6aR)-1-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furo[3,4-c]furan-3a-ol

There total 11 articles about (1S,3aS,4S,6aR)-1-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furo[3,4-c]furan-3a-ol 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%

: 195141-57-2
(2S,3S,4R)-4-(Benzo[1,3]dioxol-5-yl-hydroxy-methyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-tetrahydro-furan-3-ol

: 195141-59-4
(1S,3aS,4S,6aR)-1-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furo[3,4-c]furan-3a-ol

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; for 0.5h; Ambient temperature;
DOI:10.1271/bbb.61.1342

Reference yield:

: 195141-46-9
((2R,4R)-4-Benzo[1,3]dioxol-5-ylmethyl-3-methylene-tetrahydro-furan-2-ylmethoxy)-tert-butyl-diphenyl-silane

: 195141-59-4
(1S,3aS,4S,6aR)-1-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furo[3,4-c]furan-3a-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / OsO₄, NMO, t-BuOH / H₂O; acetone / 40 h / 0 °C

2: 88 percent / DMAP / 16 h / Ambient temperature

3: NBS, (BzO)2 / CCl₄ / 0.5 h / Heating

4: 0.27 g / SiO₂, H₂O / benzene; ethyl acetate

5: 90 percent / K₂CO₃ / methanol / 0.5 h / Ambient temperature

6: 96 percent / p-TsOH*H₂O / CH₂Cl₂ / 0.5 h / Ambient temperature

With dmap; N-Bromosuccinimide; osmium(VIII) oxide; N-methyl-2-indolinone; water; silica gel; potassium carbonate; toluene-4-sulfonic acid; tert-butyl alcohol; dibenzoyl peroxide; In methanol; tetrachloromethane; dichloromethane; water; ethyl acetate; acetone; benzene;
DOI:10.1271/bbb.61.1342

Reference yield:

: 195141-40-3
(2S,3R,4S)-4-Benzo[1,3]dioxol-5-ylmethyl-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

: 195141-59-4
(1S,3aS,4S,6aR)-1-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-dihydro-furo[3,4-c]furan-3a-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 94 percent / PCC / CH₂Cl₂ / 6 h / Ambient temperature

2: 87 percent / pyridine; tetrahydrofuran; toluene / 1 h / -40 °C

3: 99 percent / OsO₄, NMO, t-BuOH / H₂O; acetone / 40 h / 0 °C

4: 88 percent / DMAP / 16 h / Ambient temperature

5: NBS, (BzO)2 / CCl₄ / 0.5 h / Heating

6: 0.27 g / SiO₂, H₂O / benzene; ethyl acetate

7: 90 percent / K₂CO₃ / methanol / 0.5 h / Ambient temperature

8: 96 percent / p-TsOH*H₂O / CH₂Cl₂ / 0.5 h / Ambient temperature

With dmap; N-Bromosuccinimide; osmium(VIII) oxide; N-methyl-2-indolinone; water; silica gel; potassium carbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; tert-butyl alcohol; dibenzoyl peroxide; In tetrahydrofuran; pyridine; methanol; tetrachloromethane; dichloromethane; water; ethyl acetate; acetone; toluene; benzene;
DOI:10.1271/bbb.61.1342