(3aR,4R,6R,6aR)-4-Benzyloxy-6-hydroxymethyl-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-ol

Base Information

• Chemical Name: (3aR,4R,6R,6aR)-4-Benzyloxy-6-hydroxymethyl-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-ol
• CAS No.: 233668-04-7
• Molecular Formula: C₁₂H₁₅O₇P
• Molecular Weight: 302.221

Synonyms:(3aR,4R,6R,6aR)-4-Benzyloxy-6-hydroxymethyl-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-ol

Chemical Property of (3aR,4R,6R,6aR)-4-Benzyloxy-6-hydroxymethyl-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-ol

Chemical Property:

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Technology Process of (3aR,4R,6R,6aR)-4-Benzyloxy-6-hydroxymethyl-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-ol

There total 4 articles about (3aR,4R,6R,6aR)-4-Benzyloxy-6-hydroxymethyl-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-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: 42.0%

(3aR,4R,6R,6aR)-4-Benzyloxy-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-oxo-tetrahydro-2λ5-furo[3,4-d][1,3,2]dioxaphosphol-2-ol; compound with triethyl-amine → (3aR,4R,6R,6aR)-4-Benzyloxy-6-hydroxymethyl-2-oxo-tetrahydro-2λ5-furo[3,4-d][1,3,2]dioxaphosphol-2-ol (233668-04-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 25 ℃; for 4h;

Reference yield:

benzyl-β-D-ribofuranoside (54946-48-4) → (3aR,4R,6R,6aR)-4-Benzyloxy-6-hydroxymethyl-2-oxo-tetrahydro-2λ5-furo[3,4-d][1,3,2]dioxaphosphol-2-ol (233668-04-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 72 percent / pyridine / 4 h / 25 °C

2: POCl₃; pyridine / 15 h / 25 °C

3: H₂O / 1 h / 25 °C

4: 42 percent / CF₃COOH / CH₂Cl₂ / 4 h / 25 °C

With pyridine; water; trifluoroacetic acid; trichlorophosphate; In dichloromethane; 1: Substitution / 2: Esterification / 3: Hydrolysis / 4: Hydrolysis;

Reference yield:

(2R,3R,4S,5R)-2-Benzyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3,4-diol (233667-77-1) → (3aR,4R,6R,6aR)-4-Benzyloxy-6-hydroxymethyl-2-oxo-tetrahydro-2λ5-furo[3,4-d][1,3,2]dioxaphosphol-2-ol (233668-04-7)

Guidance literature:

Multi-step reaction with 3 steps

1: POCl₃; pyridine / 15 h / 25 °C

2: H₂O / 1 h / 25 °C

3: 42 percent / CF₃COOH / CH₂Cl₂ / 4 h / 25 °C

With pyridine; water; trifluoroacetic acid; trichlorophosphate; In dichloromethane; 1: Esterification / 2: Hydrolysis / 3: Hydrolysis;

upstream raw materials:

benzyl-β-D-ribofuranoside

(2R,3R,4S,5R)-2-Benzyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3,4-diol

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