(3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-4,5,6,6a-tetrahy dro-3aH-cyclopentafuran

Base Information

• Chemical Name: (3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-4,5,6,6a-tetrahy dro-3aH-cyclopentafuran
• CAS No.: 1328921-59-0
• Molecular Formula: C₂₄H₂₈O₅
• Molecular Weight: 396.483

Synonyms:(3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-4,5,6,6a-tetrahy dro-3aH-cyclopentafuran

Chemical Property of (3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-4,5,6,6a-tetrahy dro-3aH-cyclopentafuran

Chemical Property:

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Technology Process of (3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-4,5,6,6a-tetrahy dro-3aH-cyclopentafuran

There total 4 articles about (3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-4,5,6,6a-tetrahy dro-3aH-cyclopentafuran 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)-hexahydro-2H-c yclopentafuran-2-ol (1328921-52-3) → (3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-4,5,6,6a-tetrahy dro-3aH-cyclopentafuran (1328921-59-0)

Guidance literature:

(3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-hexahydro-2H-c yclopentafuran-2-ol; With triethylamine; In tetrahydrofuran; at -70 - 60 ℃; for 0.5h;

With methanesulfonyl chloride; In tetrahydrofuran; at -70 - 60 ℃; for 2h; Reflux;

Reference yield:

(3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-hexahydrocyclo pentafuran-2-one (1328921-48-7) → (3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-4,5,6,6a-tetrahy dro-3aH-cyclopentafuran (1328921-59-0)

Guidance literature:

Multi-step reaction with 2 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

With diisobutylaluminium hydride; triethylamine; In tetrahydrofuran;

Reference yield:

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one (76704-05-7) → (3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-4,5,6,6a-tetrahy dro-3aH-cyclopentafuran (1328921-59-0)

Guidance literature:

Multi-step reaction with 3 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

With tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 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,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-(hydroxymethyl)cyclopentanol

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

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

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

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