(3S,4R,4aR,8aS)-3-benzyloxy-4-hydroxy-3,4,4a,8,8a-hexahydro-1H-2-benzopyran

Base Information

• Chemical Name: (3S,4R,4aR,8aS)-3-benzyloxy-4-hydroxy-3,4,4a,8,8a-hexahydro-1H-2-benzopyran
• CAS No.: 705945-43-3
• Molecular Formula: C₁₆H₂₀O₃
• Molecular Weight: 260.333

Synonyms:(3S,4R,4aR,8aS)-3-benzyloxy-4-hydroxy-3,4,4a,8,8a-hexahydro-1H-2-benzopyran

Chemical Property of (3S,4R,4aR,8aS)-3-benzyloxy-4-hydroxy-3,4,4a,8,8a-hexahydro-1H-2-benzopyran

Chemical Property:

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Technology Process of (3S,4R,4aR,8aS)-3-benzyloxy-4-hydroxy-3,4,4a,8,8a-hexahydro-1H-2-benzopyran

There total 2 articles about (3S,4R,4aR,8aS)-3-benzyloxy-4-hydroxy-3,4,4a,8,8a-hexahydro-1H-2-benzopyran 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: 22.0%

(3S,4aR,8aS)-3-benzyloxy-4a,5,8,8a-tetrahydro-1H-2-benzopyran-4(3H)-one (391929-00-3) → (3S,4S,4aR,8aS)-3-benzyloxy-4-hydroxy-3,4,4a,5,8,8a-hexahydro-1H-2-benzopyran + (3S,4R,4aR,8aS)-3-benzyloxy-4-hydroxy-3,4,4a,8,8a-hexahydro-1H-2-benzopyran (705945-43-3)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 0.25h;

DOI:10.1016/j.carres.2004.01.008

Reference yield:

(2S)-2-benzyloxy-2H-pyran-3-(6H)-one (391928-90-8) → (3S,4R,4aR,8aS)-3-benzyloxy-4-hydroxy-3,4,4a,8,8a-hexahydro-1H-2-benzopyran (705945-43-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / BF₃*Et₂O

2: 53 percent / NaBH₄ / ethanol / 0.25 h / 0 °C

With sodium tetrahydroborate; boron trifluoride diethyl etherate; In ethanol;

DOI:10.1016/j.carres.2004.01.008

Reference yield: 53.0%

(3S,4R,4aR,8aS)-3-benzyloxy-4-hydroxy-3,4,4a,8,8a-hexahydro-1H-2-benzopyran (705945-43-3) → (1S,2S,4S,7S,8R,9R)-7-Benzyloxy-6,11-dioxa-tricyclo[6.2.1.04,9]undecan-2-ol + (3S,4R,4aR,6S,7R,8aS)-3-benzyloxy-6,7-epoxy-4-hydroxyperhydro-1H-2-benzopyran + (3S,4R,4aR,6R,7S,8aS)-3-benzyloxy-6,7-epoxy-4-hydroxyperhydro-1H-2-benzopyran

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 20 ℃; for 0.333333h;

DOI:10.1016/j.carres.2004.01.008

upstream raw materials:

(3S,4aR,8aS)-3-benzyloxy-4a,5,8,8a-tetrahydro-1H-2-benzopyran-4(3H)-one

(2S)-2-benzyloxy-2H-pyran-3-(6H)-one

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