(1R,2R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-(hydroxymethyl)cyclopentanol

Base Information

• Chemical Name: (1R,2R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-(hydroxymethyl)cyclopentanol
• CAS No.: 1355186-82-1
• Molecular Formula: C₂₃H₃₀O₆
• Molecular Weight: 402.488

Synonyms:(1R,2R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-(hydroxymethyl)cyclopentanol

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

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

There total 5 articles about (1R,2R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-(hydroxymethyl)cyclopentanol 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:

(3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-4,5,6,6a-tetrahy dro-3aH-cyclopentafuran (1328921-59-0) → (1R,2R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-(hydroxymethyl)cyclopentanol (1355186-82-1)

Guidance literature:

(3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-4,5,6,6a-tetrahy dro-3aH-cyclopentafuran; With sodium hydrogencarbonate; ozone; In methanol; dichloromethane; at -78 - 60 ℃;

With methanol; sodium tetrahydroborate; In dichloromethane; at -78 ℃; for 0.166667h;

In dichloromethane;

Reference yield:

(3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-hexahydrocyclo pentafuran-2-one (1328921-48-7) → (1R,2R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-(hydroxymethyl)cyclopentanol (1355186-82-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / Inert atmosphere

1.2: 2 h / 0 °C

2.1: triethylamine / tetrahydrofuran / 0.5 h / -70 - 60 °C

2.2: 2 h / -70 - 60 °C / Reflux

3.1: sodium hydrogencarbonate; ozone / dichloromethane; methanol / -78 - 60 °C

3.2: 0.17 h / -78 °C

With diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

Reference yield:

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one (76704-05-7) → (1R,2R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-(hydroxymethyl)cyclopentanol (1355186-82-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane

1.2: 20 °C

2.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / Inert atmosphere

2.2: 2 h / 0 °C

3.1: triethylamine / tetrahydrofuran / 0.5 h / -70 - 60 °C

3.2: 2 h / -70 - 60 °C / Reflux

4.1: sodium hydrogencarbonate; ozone / dichloromethane; methanol / -78 - 60 °C

4.2: 0.17 h / -78 °C

With tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;

upstream raw materials:

Benzyloxymethyl chloride

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

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one

(3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-hexahydro-2H-c yclopentafuran-2-ol

Downstream raw materials:

((1R,2R,3S,5R)-3-((benzyloxy)methoxy)-2-(((benzyloxy)methoxy)methyl)-5-hydroxycyclopentyl)methyl 4-methylbenzenesulfonate

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

((1R,2R,3S,5R)-3-((benzyloxy)methoxy)-2-((benzyloxymethoxy)methyl)-5-acetoxycyclopentyl)methyl 4-methylbenzenesulfonate

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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