(1S,4S,4aS,7S,7aR)-7-Benzyloxy-1,4,7a-trimethyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol

Base Information

Chemical Name:(1S,4S,4aS,7S,7aR)-7-Benzyloxy-1,4,7a-trimethyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol
CAS No.:71686-31-2
Molecular Formula:C₁₈H₂₄O₃
Molecular Weight:288.387
Hs Code.:

Synonyms:(1S,4S,4aS,7S,7aR)-7-Benzyloxy-1,4,7a-trimethyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol

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Chemical Property of (1S,4S,4aS,7S,7aR)-7-Benzyloxy-1,4,7a-trimethyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol

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Technology Process of (1S,4S,4aS,7S,7aR)-7-Benzyloxy-1,4,7a-trimethyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol

There total 7 articles about (1S,4S,4aS,7S,7aR)-7-Benzyloxy-1,4,7a-trimethyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-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:

: 82043-27-4
(1β,4α,4aα,7β,7aβ)-4,4a,7,7a-tetrahydro-1,4,7a-trimethyl-7-(phenylmethoxy)cyclopentapyran-3(1H)-one

: 71686-31-2
(1S,4S,4aS,7S,7aR)-7-Benzyloxy-1,4,7a-trimethyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.5h;
DOI:10.1021/ja00379a030

Reference yield:

: 100-39-0
benzyl bromide

: 71686-31-2
(1S,4S,4aS,7S,7aR)-7-Benzyloxy-1,4,7a-trimethyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / NaH, Bu₄NI / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) 0 deg C, 30 min, 2.) room temperature, 1 h, 3.) 50 deg C, 12 h

2: p-toluenesulfonic acid / methanol / 2 h / Ambient temperature

3: 89 percent / 10percent aq. KOH / methanol / 21 h / 55 °C

4: 64 percent / p-toluenesulfonyl chloride, DBU / toluene / 1.) 0 deg C, 15 min, 2.) ambient temperature, 1 h

5: 92 percent / DBU / toluene / 3 h / Heating

6: i-Bu₂AlH / toluene / 0.5 h / -78 °C

With potassium hydroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; toluene;
DOI:10.1021/ja00379a030

Reference yield:

: 82043-30-9
α,5-dimethyl-4-(phenylmethoxy)-5-(1-hydroxyethyl)-2-cyclopentene-1-acetic acid

: 71686-31-2
(1S,4S,4aS,7S,7aR)-7-Benzyloxy-1,4,7a-trimethyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 64 percent / p-toluenesulfonyl chloride, DBU / toluene / 1.) 0 deg C, 15 min, 2.) ambient temperature, 1 h

2: 92 percent / DBU / toluene / 3 h / Heating

3: i-Bu₂AlH / toluene / 0.5 h / -78 °C

With diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride; In toluene;
DOI:10.1021/ja00379a030