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

Base Information

• Chemical Name: (3aS,4R,5S,7aR)-4-(benzyloxy)-2-oxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ⁴-1,3,2-benzodioxathiol-5-ol
• CAS No.: 691371-41-2
• Molecular Formula: C₅₃H₄₈O₇S
• Molecular Weight: 829.026

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

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

Chemical Property:

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

There total 3 articles about (3aS,4R,5S,7aR)-4-(benzyloxy)-2-oxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ⁴-1,3,2-benzodioxathiol-5-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: 90.0%

(1R,2R,3R,4S)-3-(benzyloxy)-5,5-bis[(trityloxy)methyl]cyclohexane-1,2,4-triol (691371-40-1) → (3aS,4R,5S,7aR)-4-(benzyloxy)-2-oxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ4-1,3,2-benzodioxathiol-5-ol (691371-41-2)

Guidance literature:

With thionyl chloride; triethylamine; In diethyl ether; at -75 - -20 ℃; for 4h;

DOI:10.1135/cccc20040435

Reference yield:

trityl chloride (76-83-5) → (3aS,4R,5S,7aR)-4-(benzyloxy)-2-oxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ4-1,3,2-benzodioxathiol-5-ol (691371-41-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine; thionyl chloride; triethylamine; In diethyl ether;

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-oxo-6,6-bis[(trityloxy)methyl]hexahydro-2λ4-1,3,2-benzodioxathiol-5-ol (691371-41-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With pyridine; thionyl chloride; triethylamine; In diethyl ether;

DOI:10.1135/cccc20040435

upstream raw materials:

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

trityl chloride

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

Downstream raw materials:

(1R,2R,3S,6S)-6-[(5-amino-6-chloropyrimidin-4-yl)amino]-2-(benzyloxy)-4,4-bis[(trityloxy)methyl]cyclohexane-1,3-diol

(1S,4R,5S,6S)-5-[(5-amino-6-chloropyrimidin-4-yl)amino]-6-(benzyloxy)-2,2-bis[(trityloxy)methyl]cyclohexane-1,4-diol

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

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

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