(2S,4aS,6S,7R,9aR)-6-(2-Hydroxy-ethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

Base Information

Chemical Name:(2S,4aS,6S,7R,9aR)-6-(2-Hydroxy-ethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol
CAS No.:213766-75-7
Molecular Formula:C₁₇H₂₄O₅
Molecular Weight:308.375
Hs Code.:

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

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Chemical Property of (2S,4aS,6S,7R,9aR)-6-(2-Hydroxy-ethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

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Technology Process of (2S,4aS,6S,7R,9aR)-6-(2-Hydroxy-ethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

There total 13 articles about (2S,4aS,6S,7R,9aR)-6-(2-Hydroxy-ethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-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: 100.0%

: 213766-72-4
2-[(2S,4aS,6S,7R,9aR)-7-(tert-Butyl-dimethyl-silanyloxy)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-6-yl]-ethanol

: 213766-75-7
(2S,4aS,6S,7R,9aR)-6-(2-Hydroxy-ethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;
DOI:10.1016/S0040-4039(98)01311-2

Reference yield:

: 213765-97-0
(4R,5S)-2,2-Dimethyl-4-hydroxymethyl-5-((E)-methoxycarbonylethenyl)-1,3-dioxolane

: 213766-75-7
(2S,4aS,6S,7R,9aR)-6-(2-Hydroxy-ethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

Guidance literature:: Multi-step reaction with 12 steps

1: 83 percent / H₂ / 10 percent Pd/C / methanol / Ambient temperature

2: 99 percent / imidazole / dimethylformamide / 0 deg C -> RT

3: 96 percent / LiAlH₄ / tetrahydrofuran / 0 °C

4: 98 percent / imidazole / dimethylformamide / 0 deg C -> RT

5: 73 percent / PdCl₂(CH₃CN)2 / acetonitrile / Ambient temperature

6: 85 percent / CSA / CH₂Cl₂ / Ambient temperature

7: 1.) (COCl)2, 2.) Et₃N / 1.) DMSO/CH₂Cl₂, -78 deg C, 2.) DMSO/CH₂Cl₂, -78 deg C -> RT, 3.) toluene, -78 deg C

8: 100 percent / KH / tetrahydrofuran / 0 deg C -> RT

9: 1.) n-Bu₃SnCl, sec-BuLi, TMEDA, 2.) TBAF, 3.) SO₃*pyridine, DMSO, Et₃N, 4.) BF₃*EtO₂

10: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

11: 99 percent / (cyc-Hex)2BH / tetrahydrofuran / 0 °C

12: 100 percent / TBAF / tetrahydrofuran / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; dichloro bis(acetonitrile) palladium(II); lithium aluminium tetrahydride; oxalyl dichloride; pyridine-SO₃ complex; N,N,N,N,-tetramethylethylenediamine; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; tributyltin chloride; tetrabutyl ammonium fluoride; hydrogen; sec.-butyllithium; potassium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(98)01311-2

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 213766-75-7
(2S,4aS,6S,7R,9aR)-6-(2-Hydroxy-ethyl)-4a-methyl-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / CSA / CH₂Cl₂ / Ambient temperature

2: 1.) (COCl)2, 2.) Et₃N / 1.) DMSO/CH₂Cl₂, -78 deg C, 2.) DMSO/CH₂Cl₂, -78 deg C -> RT, 3.) toluene, -78 deg C

3: 100 percent / KH / tetrahydrofuran / 0 deg C -> RT

4: 1.) n-Bu₃SnCl, sec-BuLi, TMEDA, 2.) TBAF, 3.) SO₃*pyridine, DMSO, Et₃N, 4.) BF₃*EtO₂

5: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

6: 99 percent / (cyc-Hex)2BH / tetrahydrofuran / 0 °C

7: 100 percent / TBAF / tetrahydrofuran / Ambient temperature

With 2,6-dimethylpyridine; oxalyl dichloride; pyridine-SO₃ complex; N,N,N,N,-tetramethylethylenediamine; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; tributyltin chloride; tetrabutyl ammonium fluoride; sec.-butyllithium; potassium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4039(98)01311-2