(3aS,6R,7S,7aR)-1-Benzyl-6-hydroxymethyl-6-methyl-hexahydro-pyrano[4,3-c]isoxazol-7-ol

Base Information

• Chemical Name: (3aS,6R,7S,7aR)-1-Benzyl-6-hydroxymethyl-6-methyl-hexahydro-pyrano[4,3-c]isoxazol-7-ol
• CAS No.: 595566-36-2
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.336

Synonyms:(3aS,6R,7S,7aR)-1-Benzyl-6-hydroxymethyl-6-methyl-hexahydro-pyrano[4,3-c]isoxazol-7-ol

Chemical Property of (3aS,6R,7S,7aR)-1-Benzyl-6-hydroxymethyl-6-methyl-hexahydro-pyrano[4,3-c]isoxazol-7-ol

Chemical Property:

Purity/Quality:

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Technology Process of (3aS,6R,7S,7aR)-1-Benzyl-6-hydroxymethyl-6-methyl-hexahydro-pyrano[4,3-c]isoxazol-7-ol

There total 5 articles about (3aS,6R,7S,7aR)-1-Benzyl-6-hydroxymethyl-6-methyl-hexahydro-pyrano[4,3-c]isoxazol-7-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: 73.0%

(3aS,6S,7S,7aR)-1-Benzyl-7-hydroxy-6-methyl-hexahydro-pyrano[4,3-c]isoxazole-6-carbaldehyde (595566-35-1) → (3aS,6R,7S,7aR)-1-Benzyl-6-hydroxymethyl-6-methyl-hexahydro-pyrano[4,3-c]isoxazol-7-ol (595566-36-2)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 25 ℃; for 3h;

DOI:10.1016/S0040-4020(03)00634-3

Reference yield:

N-benzyl hydroxylalmine (622-30-0) → (3aS,6R,7S,7aR)-1-Benzyl-6-hydroxymethyl-6-methyl-hexahydro-pyrano[4,3-c]isoxazol-7-ol (595566-36-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,2,2-trifluoro-ethanol / Heating

2: 65 percent / NaIO₄ / methanol / 2 h / 25 °C

3: 73 percent / NaBH₄ / ethanol / 3 h / 25 °C

With sodium tetrahydroborate; sodium periodate; In methanol; ethanol; 2,2,2-trifluoroethanol;

DOI:10.1016/S0040-4020(03)00634-3

Reference yield:

(3R,4R,5R,6R)-4-Allyloxy-6-hydroxymethyl-4-methyl-tetrahydro-pyran-2,3,5-triol → (3aS,6R,7S,7aR)-1-Benzyl-6-hydroxymethyl-6-methyl-hexahydro-pyrano[4,3-c]isoxazol-7-ol (595566-36-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,2,2-trifluoro-ethanol / Heating

2: 65 percent / NaIO₄ / methanol / 2 h / 25 °C

3: 73 percent / NaBH₄ / ethanol / 3 h / 25 °C

With sodium tetrahydroborate; sodium periodate; In methanol; ethanol; 2,2,2-trifluoroethanol;

DOI:10.1016/S0040-4020(03)00634-3

upstream raw materials:

(3aS,6S,7S,7aR)-1-Benzyl-7-hydroxy-6-methyl-hexahydro-pyrano[4,3-c]isoxazole-6-carbaldehyde

N-benzyl hydroxylalmine

(3aS,6S,7S,7aR)-7-acetoxy-1-benzyl-6-methyl-6-[((1R,2R)-1,2,3-triacetoxy)prop-1-yl]-1,3,3a,6,7,7a-hexahydro-4H-pyrano[4,5-c]isoxazole

(1R,2R)-1-((3aS,6S,7S,7aR)-1-Benzyl-7-hydroxy-6-methyl-hexahydro-pyrano[4,3-c]isoxazol-6-yl)-propane-1,2,3-triol

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