(4R,4aR,5S,8S,8aR)-5,8-Bis-benzyloxy-4-[3-(1-ethoxy-ethoxy)-propyl]-3-methylene-octahydro-naphthalen-2-one

Base Information

Chemical Name:(4R,4aR,5S,8S,8aR)-5,8-Bis-benzyloxy-4-[3-(1-ethoxy-ethoxy)-propyl]-3-methylene-octahydro-naphthalen-2-one
CAS No.:79782-45-9
Molecular Formula:C₃₂H₄₂O₅
Molecular Weight:506.682
Hs Code.:

Synonyms:(4R,4aR,5S,8S,8aR)-5,8-Bis-benzyloxy-4-[3-(1-ethoxy-ethoxy)-propyl]-3-methylene-octahydro-naphthalen-2-one

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Chemical Property of (4R,4aR,5S,8S,8aR)-5,8-Bis-benzyloxy-4-[3-(1-ethoxy-ethoxy)-propyl]-3-methylene-octahydro-naphthalen-2-one

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Technology Process of (4R,4aR,5S,8S,8aR)-5,8-Bis-benzyloxy-4-[3-(1-ethoxy-ethoxy)-propyl]-3-methylene-octahydro-naphthalen-2-one

There total 22 articles about (4R,4aR,5S,8S,8aR)-5,8-Bis-benzyloxy-4-[3-(1-ethoxy-ethoxy)-propyl]-3-methylene-octahydro-naphthalen-2-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:

: 79782-44-8
Methanesulfonic acid (1R,4aR,5S,8S,8aR)-5,8-bis-benzyloxy-1-[3-(1-ethoxy-ethoxy)-propyl]-3-oxo-decahydro-naphthalen-2-ylmethyl ester

: 79782-45-9
(4aα,8aβ)-5β,8α-bis(benzyloxy)-2-methylene-3-oxo-1β-<3-(1-ethoxyethoxy)propyl>decahydronaphthalene

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; at 25 ℃; for 1h;
DOI:10.1021/ja00341a046

Reference yield:

: 79782-44-8
Methanesulfonic acid (1R,4aR,5S,8S,8aR)-5,8-bis-benzyloxy-1-[3-(1-ethoxy-ethoxy)-propyl]-3-oxo-decahydro-naphthalen-2-ylmethyl ester

: 79782-45-9
(4R,4aR,5S,8S,8aR)-5,8-Bis-benzyloxy-4-[3-(1-ethoxy-ethoxy)-propyl]-3-methylene-octahydro-naphthalen-2-one

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; at 25 ℃; Yield given;
DOI:10.1021/ja00411a063

Reference yield:

: 2906-93-6,3198-51-4,6102-42-7,36159-09-8,54963-84-7,84275-37-6
(+/-)-1,4,5,8,9,10-trans-hexahydronaphthalene-1,4-dione

: 79782-45-9
(4aα,8aβ)-5β,8α-bis(benzyloxy)-2-methylene-3-oxo-1β-<3-(1-ethoxyethoxy)propyl>decahydronaphthalene

Guidance literature:: Multi-step reaction with 10 steps

1: 18.67 g / Aureobasidium pullulans NRRL Y-12610 / H₂O / 72 °C

2: 99 percent / 1.) NaH / dimethylsulfoxide / 1.) RT, 30 min, 2.) RT, 3 h

3: 32 g / acetic acid / 1 h / 25 °C

4: 88 percent / 4percent KOH / methanol; diethyl ether / 2 h / 25 °C

5: 30percent H₂O₂ / tetrahydrofuran; H₂O / 2.5 h / 25 °C

6: tetrahydrofuran; H₂O / 2 h / 55 °C

7: 20.6 g / Jones reagent / tetrahydrofuran; H₂O; acetone / 0.25 h

8: 1.) THF, -20 deg C, 30 min, 2.) -78 deg C

9: 38 g / Et₃N / CH₂Cl₂ / 0.5 h / -5 °C

10: 28.09 g / DBU / benzene / 1 h / 25 °C

With potassium hydroxide; jones reagent; Aureobasidium pullulans NRRL Y-12610; dihydrogen peroxide; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; dimethyl sulfoxide; acetone; benzene;
DOI:10.1021/ja00341a046