(1R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopent anol

Base Information

• Chemical Name: (1R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopent anol
• CAS No.: 1328921-71-6
• Molecular Formula: C₂₃H₂₈O₅
• Molecular Weight: 384.472

Synonyms:(1R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopent anol

Chemical Property of (1R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopent anol

Chemical Property:

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Technology Process of (1R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopent anol

There total 11 articles about (1R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopent anol 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:

((1R,2R,3S,5R)-3-((benzyloxy)methoxy)-2-((benzyloxymethoxy)methyl)-5-acetoxycyclopentyl)methyl 4-methylbenzenesulfonate (1328921-70-5) → (1R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopent anol (1328921-71-6)

Guidance literature:

((1R,2R,3S,5R)-3-((benzyloxy)methoxy)-2-((benzyloxymethoxy)methyl)-5-acetoxycyclopentyl)methyl 4-methylbenzenesulfonate; With lithium iodide; In N,N-dimethyl acetamide; at 20 - 100 ℃; for 1.5h;

1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl acetamide; at 90 - 100 ℃; for 16h;

With hydrogenchloride; In N,N-dimethyl acetamide; water;

Reference yield:

C24H28O6 (1328921-76-1) → (1R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopent anol (1328921-71-6)

Guidance literature:

C₂₄H₂₈O₆; With methanol; sodium hydroxide; at 20 ℃; for 1h;

With hydrogenchloride;

Reference yield:

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one (76704-05-7) → (1R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopent anol (1328921-71-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid / 2 h / 20 °C

2.1: diisobutylaluminium hydride / toluene / 1 h / -78 - -60 °C / Inert atmosphere

2.2: 1.5 h / 0 °C

3.1: palladium diacetate; copper diacetate / 8 h / 20 °C / Reflux

4.1: sodium hydroxide; methanol / 1 h / 20 °C

With methanol; diisobutylaluminium hydride; toluene-4-sulfonic acid; sodium hydroxide; copper diacetate; palladium diacetate; In toluene;

upstream raw materials:

Benzyloxymethyl chloride

(3aS,4R,5S,6aR)-hexahydro-5-(methoxymethoxy)-4-((methoxymethoxy)methyl)cyclopenta[b]furan-2-one

(3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-hexahydrocyclo pentafuran-2-one

(3aS,4R,5S,6aR)-hexahydro-5-(methoxymethoxy)-4-((methoxymethoxy)methyl)-2H-cyclopenta[b]furan-2-ol

Downstream raw materials:

tert-butyl 9-((1S,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopentyl)-6-iodo-9H-purin-2-ylcarbamate

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