(2R,4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene

Base Information

Chemical Name:(2R,4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene
CAS No.:440333-96-0
Molecular Formula:C₃₀H₃₄O₅
Molecular Weight:474.597
Hs Code.:

Synonyms:(2R,4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene

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Chemical Property of (2R,4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene

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Technology Process of (2R,4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene

There total 7 articles about (2R,4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene 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: 68.0%

: 100-39-0
benzyl bromide

: 440333-65-3
(2R,4aR,6S,7R,9aS)-6-Hydroxymethyl-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

: 440333-96-0
(2R,4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene

Guidance literature:: With potassium hydride; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

: (2R,4aR,6S,7R,8aS)-4a-Methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 440333-96-0
(2R,4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene

Guidance literature:: Multi-step reaction with 7 steps

1.1: O₃ / methanol / -78 °C

1.2: 78 percent / NaBH₄ / methanol / -78 - 20 °C

2.1: 86 percent / imidazole / dimethylformamide / 20 °C

3.1: DMSO; (COCl)2 / CH₂Cl₂ / -78 °C

3.2: 93 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: BF₃*OEt₂ / CH₂Cl₂ / -78 °C

4.2: 74 percent / PPTS / methanol / 20 °C

5.1: 89 percent / TBAF / tetrahydrofuran / 20 °C

6.1: 89 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / -20 °C

7.1: 68 percent / KH / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium hydride; ozone; dimethyl sulfoxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; 3.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)00039-X

Reference yield:

: 440333-93-7
(2R,4aR,6S,7R,8aS)-6-Hydroxymethyl-4a-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

: 440333-96-0
(2R,4aR,6S,7R,9aS)-7-Benzyloxy-6-benzyloxymethyl-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene

Guidance literature:: Multi-step reaction with 6 steps

1.1: 86 percent / imidazole / dimethylformamide / 20 °C

2.1: DMSO; (COCl)2 / CH₂Cl₂ / -78 °C

2.2: 93 percent / Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: BF₃*OEt₂ / CH₂Cl₂ / -78 °C

3.2: 74 percent / PPTS / methanol / 20 °C

4.1: 89 percent / TBAF / tetrahydrofuran / 20 °C

5.1: 89 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / -20 °C

6.1: 68 percent / KH / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; potassium hydride; dimethyl sulfoxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; 2.1: Swern oxidation;
DOI:10.1016/S0040-4020(02)00039-X