(3aR,6R,6aR)-6-((S)-2-(benzyloxy)-1-hydroxyethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

Base Information

• Chemical Name: (3aR,6R,6aR)-6-((S)-2-(benzyloxy)-1-hydroxyethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one
• CAS No.: 90700-15-5
• Molecular Formula: C₁₆H₂₀O₆
• Molecular Weight: 308.331

Synonyms:(3aR,6R,6aR)-6-((S)-2-(benzyloxy)-1-hydroxyethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

Chemical Property of (3aR,6R,6aR)-6-((S)-2-(benzyloxy)-1-hydroxyethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

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Technology Process of (3aR,6R,6aR)-6-((S)-2-(benzyloxy)-1-hydroxyethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

There total 13 articles about (3aR,6R,6aR)-6-((S)-2-(benzyloxy)-1-hydroxyethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-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: 96.0%

(3aR,6S,6aR)-6-[(S)-2-Benzyloxy-1-(methyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-dihydro-furo[3,4-d][1,3]dioxol-4-one (90661-47-5) → (3aR,6R,6aR)-6-((S)-2-(benzyloxy)-1-hydroxyethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one (90700-15-5)

Guidance literature:

With ammonium fluoride; tetra(n-butyl)ammonium hydrogensulfate; In water; ethyl acetate;

DOI:10.1016/S0040-4020(01)97597-0

Reference yield: 90.0%

(3R,4S,5R)-5-((S)-2'-(benzyloxy)-1'-hydroxyethyl)-3,4-dihydroxy-4,5-dihydrofuran-2(3H)-one + 2,2-dimethoxy-propane (77-76-9) → (3aR,6R,6aR)-6-((S)-2-(benzyloxy)-1-hydroxyethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one (90700-15-5)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1039/c4ra06884j

Reference yield: 80.0%

(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 (872326-54-0) → (3aR,6R,6aR)-6-((S)-2-(benzyloxy)-1-hydroxyethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one (90700-15-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1021/jo051476+

upstream raw materials:

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

(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

(2Z,4E)-ethyl 6-(benzyloxy)hexa-2,4-dienoate

(S)-5-((S)-2'-(benzyloxy)-1'-(tert-butyl(dimethyl)silanyloxy)ethyl)furan-2(5H)-one

Downstream raw materials:

(3aR,6R,6aR)-6-((R)-1-azido-2-(benzyloxy)ethyl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one

Acetic acid (2R,3R,4R)-4,5-diacetoxy-2-((R)-1-azido-2-benzyloxy-ethyl)-tetrahydro-furan-3-yl ester

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-((R)-1-azido-2-benzyloxy-ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

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