(3aR,6S,6aR)-6-[(S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one

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Chemical Name:(3aR,6S,6aR)-6-[(S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one
CAS No.:872326-54-0
Molecular Formula:C₂₂H₃₄O₆Si
Molecular Weight:422.594
Hs Code.:

Synonyms:(3aR,6S,6aR)-6-[(S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one

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Chemical Property of (3aR,6S,6aR)-6-[(S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one

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Technology Process of (3aR,6S,6aR)-6-[(S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one

There total 4 articles about (3aR,6S,6aR)-6-[(S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-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%

: 872326-51-7
(3R,4S,5S)-5-((S)-2'-(benzyloxy)-1'-(tert-butyl(dimethyl)silanyloxy)ethyl)-3,4-dihydroxy-4,5-dihydrofuran-2(3H)-one

: 77-76-9
2,2-dimethoxy-propane

: 872326-54-0
(3aR,6S,6aR)-6-[(S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one

Guidance literature:: With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1021/jo051476+

Reference yield:

: 872326-43-7
(2Z,4E)-ethyl 6-(benzyloxy)hexa-2,4-dienoate

: 872326-54-0
(3aR,6S,6aR)-6-[(S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: K₃Fe(CN)6; K₂CO₃; OsO₄ / (DHQ)2PHAL; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 0 °C

1.2: imidazole / dimethylformamide / 12 h / 20 °C

2.1: NMO; OsO₄ / methanol; H₂O / 0 °C

3.1: 87 percent / CSA / CH₂Cl₂ / 3 h / 20 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; camphor-10-sulfonic acid; potassium carbonate; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; In methanol; dichloromethane; water; tert-butyl alcohol; 1.1: Sharpless dihydroxylation / 2.1: Sharpless dihydroxylation;
DOI:10.1021/jo051476+

Reference yield:

: 69152-87-0
4-benzyloxycrotonaldehyde

: 872326-54-0
(3aR,6S,6aR)-6-[(S)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: t-BuOK / 18-crown-6 / tetrahydrofuran / 0.25 h / -78 °C

1.2: tetrahydrofuran / 2.5 h / -78 °C

2.1: K₃Fe(CN)6; K₂CO₃; OsO₄ / (DHQ)2PHAL; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 0 °C

2.2: imidazole / dimethylformamide / 12 h / 20 °C

3.1: NMO; OsO₄ / methanol; H₂O / 0 °C

4.1: 87 percent / CSA / CH₂Cl₂ / 3 h / 20 °C

With osmium(VIII) oxide; N-methyl-2-indolinone; camphor-10-sulfonic acid; potassium tert-butylate; potassium carbonate; potassium hexacyanoferrate(III); Hydroquinone 1,4-phthalazinediyl diether; 18-crown-6 ether; methanesulfonamide; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; 2.1: Sharpless dihydroxylation / 3.1: Sharpless dihydroxylation;
DOI:10.1021/jo051476+