6-benzyloxymethyl-5-bromo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

Base Information

• Chemical Name: 6-benzyloxymethyl-5-bromo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol
• CAS No.: 643760-42-3
• Molecular Formula: C₁₆H₁₉BrO₄
• Molecular Weight: 355.228

Synonyms:6-benzyloxymethyl-5-bromo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

Chemical Property of 6-benzyloxymethyl-5-bromo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

Chemical Property:

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Technology Process of 6-benzyloxymethyl-5-bromo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol

There total 2 articles about 6-benzyloxymethyl-5-bromo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-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: 78.0%

6-benzyloxymethyl-5-bromo-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one (643760-52-5) → 6-benzyloxymethyl-5-bromo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol (643760-42-3)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In methanol; at 0 ℃; stereoselective reaction;

DOI:10.1021/jm1010836

Reference yield:

(3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one (117307-62-7,89291-75-8) → 6-benzyloxymethyl-5-bromo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol (643760-42-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Br₂; pyridine / CCl₄

2: NaBH₄; CeCl₃*7H₂O

With pyridine; sodium tetrahydroborate; cerium(III) chloride; bromine; In tetrachloromethane;

DOI:10.1081/NCN-120021961

Reference yield: 95.0%

methanesulfonyl chloride (124-63-0) + 6-benzyloxymethyl-5-bromo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-ol (643760-42-3) → methanesulfonic acid 6-benzyloxymethyl-5-bromo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester (643760-43-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jm1010836

upstream raw materials:

6-benzyloxymethyl-5-bromo-2,2-dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

(3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one

Downstream raw materials:

methanesulfonic acid 6-benzyloxymethyl-5-bromo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester

9-(6-benzyloxymethyl-5-bromo-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-9H-purin-6-ylamine

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