(3aS,4R,5S,7aR)-4-(benzyloxy)-2,2-dioxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ⁴-1,3,2-benzodioxathiol-5-yl benzoate

Base Information

• Chemical Name: (3aS,4R,5S,7aR)-4-(benzyloxy)-2,2-dioxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ⁴-1,3,2-benzodioxathiol-5-yl benzoate
• CAS No.: 691371-42-3
• Molecular Formula: C₆₀H₅₂O₉S
• Molecular Weight: 949.133

Synonyms:(3aS,4R,5S,7aR)-4-(benzyloxy)-2,2-dioxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ⁴-1,3,2-benzodioxathiol-5-yl benzoate

Chemical Property of (3aS,4R,5S,7aR)-4-(benzyloxy)-2,2-dioxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ⁴-1,3,2-benzodioxathiol-5-yl benzoate

Chemical Property:

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Technology Process of (3aS,4R,5S,7aR)-4-(benzyloxy)-2,2-dioxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ⁴-1,3,2-benzodioxathiol-5-yl benzoate

There total 5 articles about (3aS,4R,5S,7aR)-4-(benzyloxy)-2,2-dioxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ⁴-1,3,2-benzodioxathiol-5-yl benzoate 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:

Benzoic acid (3aS,4R,5S,7aR)-4-benzyloxy-2-oxo-6,6-bis-trityloxymethyl-hexahydro-2λ4-benzo[1,3,2]dioxathiol-5-yl ester → (3aS,4R,5S,7aR)-4-(benzyloxy)-2,2-dioxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ4-1,3,2-benzodioxathiol-5-yl benzoate (691371-42-3)

Guidance literature:

With ruthenium trichloride; potassium metaperiodate; In tetrachloromethane; acetonitrile; at 0 - 20 ℃; for 1h;

DOI:10.1135/cccc20040435

Reference yield:

trityl chloride (76-83-5) → (3aS,4R,5S,7aR)-4-(benzyloxy)-2,2-dioxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ4-1,3,2-benzodioxathiol-5-yl benzoate (691371-42-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / pyridine / 1 h / 100 °C

2: 90 percent / thionyl chloride; Et₃N / diethyl ether / 4 h / -75 - -20 °C

3: pyridine / 20 °C

4: 4.95 g / aq. potassium periodate; RuCl₃ / CCl₄; acetonitrile / 1 h / 0 - 20 °C

With pyridine; ruthenium trichloride; thionyl chloride; potassium metaperiodate; triethylamine; In tetrachloromethane; diethyl ether; acetonitrile;

DOI:10.1135/cccc20040435

Reference yield:

(1R,2R,3R,4S)-3-(Benzyloxy)-5,5-bis(hydroxymethyl)cyclohexane-1,2,4-triol (360562-15-8) → (3aS,4R,5S,7aR)-4-(benzyloxy)-2,2-dioxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ4-1,3,2-benzodioxathiol-5-yl benzoate (691371-42-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / pyridine / 1 h / 100 °C

2: 90 percent / thionyl chloride; Et₃N / diethyl ether / 4 h / -75 - -20 °C

3: pyridine / 20 °C

4: 4.95 g / aq. potassium periodate; RuCl₃ / CCl₄; acetonitrile / 1 h / 0 - 20 °C

With pyridine; ruthenium trichloride; thionyl chloride; potassium metaperiodate; triethylamine; In tetrachloromethane; diethyl ether; acetonitrile;

DOI:10.1135/cccc20040435

upstream raw materials:

trityl chloride

(1R,2R,3R,4S)-3-(Benzyloxy)-5,5-bis(hydroxymethyl)cyclohexane-1,2,4-triol

(1R,2R,3R,4S)-3-(benzyloxy)-5,5-bis[(trityloxy)methyl]cyclohexane-1,2,4-triol

(3aS,4R,5S,7aR)-4-(benzyloxy)-2-oxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ⁴-1,3,2-benzodioxathiol-5-ol

Downstream raw materials:

(1S,4S,5R,6S)-4-(6-amino-9H-purin-9-yl)-5-hydroxy-2,2-bis(hydroxymethyl)-6-(benzyloxy)cyclohexyl benzoate

(1S,4S,5R,6S)-4-azido-5-hydroxy-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]cyclohexyl benzoate

(1R,2R,3S,6S)-6-(6-amino-9H-purin-9-yl)-2-(benzyloxy)-4,4-bis(hydroxymethyl)cyclohexane-1,3-diol

(1R,2R,3S,6S)-6-[(2-amino-6-chloropyrimidin-4-yl)amino]-4,4-bis(hydroxymethyl)-2-(benzyloxy)cyclohexane-1,3-diol

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