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

Base Information

• Chemical Name: (3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-hexahydrocyclo pentafuran-2-one
• CAS No.: 1328921-48-7
• Molecular Formula: C₂₄H₂₈O₆
• Molecular Weight: 412.483

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

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

Chemical Property:

Purity/Quality:

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

There total 1 articles about (3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-hexahydrocyclo pentafuran-2-one 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:

Benzyloxymethyl chloride (3587-60-8) + <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)-hexahydrocyclo pentafuran-2-one (1328921-48-7)

Guidance literature:

<3aS(3aα,4α,5β,6aα)>-(+)-5-hydroxy-4-hydroxymethyl-hexahydro-2H-cyclopentafuran-2-one; With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In dichloromethane;

Benzyloxymethyl chloride; In dichloromethane; at 20 ℃;

With hydrogenchloride; In dichloromethane; water;

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)-hexahydro-2H-c yclopentafuran-2-ol (1328921-52-3)

Guidance literature:

(3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-hexahydrocyclo pentafuran-2-one; With diisobutylaluminium hydride; In tetrahydrofuran; for 1h; Inert atmosphere;

With water; In tetrahydrofuran; methanol; at 0 ℃; for 2h;

Reference yield:

(3aS,4R,5S,6aR)-5-((benzyloxy)methoxy)-4-(((benzyloxy)methoxy)methyl)-hexahydrocyclo pentafuran-2-one (1328921-48-7) → (1R,3R,4S)-4-((benzyloxy)methoxy)-3-(((benzyloxy)methoxy)methyl)-2-methylenecyclopent anol (1328921-71-6)

Guidance literature:

Multi-step reaction with 6 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

4.1: pyridine / dichloromethane / 0.5 h / 50 °C

4.2: 1 h / 0 - 20 °C

4.3: 0 - 10 °C

5.1: dmap / dichloromethane / 0.5 h / 0 - 10 °C

5.2: 2 h / 20 °C

6.1: lithium iodide / N,N-dimethyl acetamide / 1.5 h / 20 - 100 °C

6.2: 16 h / 90 - 100 °C

With pyridine; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; triethylamine; lithium iodide; dmap; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl acetamide;

upstream raw materials:

Benzyloxymethyl chloride

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

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

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

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

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