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

Base Information

Chemical Name:(3S,4aR,5S,8R,8aS)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-ethano-1H-2-benzopyran-4(3H)-one
CAS No.:476487-90-8
Molecular Formula:C₁₈H₂₀O₃
Molecular Weight:284.355
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4aR,5S,8R,8aS)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-ethano-1H-2-benzopyran-4(3H)-one

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Technology Process of (3S,4aR,5S,8R,8aS)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-ethano-1H-2-benzopyran-4(3H)-one

There total 8 articles about (3S,4aR,5S,8R,8aS)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-ethano-1H-2-benzopyran-4(3H)-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: 65.0%

: 1165952-91-9
cyclohexa-1,3-diene

: 391928-90-8
(2S)-2-benzyloxy-2H-pyran-3-(6H)-one

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

: 476487-90-8
(3S,4aR,5S,8R,8aS)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-ethano-1H-2-benzopyran-4(3H)-one

Guidance literature:: With hydroquinone; In toluene; at 130 ℃; for 110h;
DOI:10.1021/jo020309w

Reference yield:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
D-Xylose

: 476487-90-8
(3S,4aR,5S,8R,8aS)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-ethano-1H-2-benzopyran-4(3H)-one

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / 16 h / 0 °C

2: HBr / H₂O; acetic acid / 1 h / 0 °C

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.33 h / -18 °C

4: 82 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / 5 °C

5: 65 percent / hydroquinone / toluene / 110 h / 130 °C

With pyridine; boron trifluoride diethyl etherate; hydrogen bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; hydroquinone; In dichloromethane; water; acetic acid; toluene;
DOI:10.1021/jo020309w

Reference yield:

: 50837-92-8
2,3,4-tri-O-acetyl-D-xylopyranosyl bromide

: 476487-90-8
(3S,4aR,5S,8R,8aS)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-ethano-1H-2-benzopyran-4(3H)-one

Guidance literature:: Multi-step reaction with 3 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.33 h / -18 °C

2: 82 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / 5 °C

3: 65 percent / hydroquinone / toluene / 110 h / 130 °C

With boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; hydroquinone; In dichloromethane; toluene;
DOI:10.1021/jo020309w