1β,4α-bis(benzyloxy)-1,2,3,4,4aβ,5,8,8aα-octahydronaphthalene

Base Information

• Chemical Name: 1β,4α-bis(benzyloxy)-1,2,3,4,4aβ,5,8,8aα-octahydronaphthalene
• CAS No.: 84131-75-9
• Molecular Formula: C₂₄H₂₈O₂
• Molecular Weight: 348.485
• Mol file: 84131-75-9.mol

Synonyms:1β,4α-bis(benzyloxy)-1,2,3,4,4aβ,5,8,8aα-octahydronaphthalene

Chemical Property of 1β,4α-bis(benzyloxy)-1,2,3,4,4aβ,5,8,8aα-octahydronaphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1β,4α-bis(benzyloxy)-1,2,3,4,4aβ,5,8,8aα-octahydronaphthalene

There total 2 articles about 1β,4α-bis(benzyloxy)-1,2,3,4,4aβ,5,8,8aα-octahydronaphthalene 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: 99.0%

benzyl chloride (100-44-7) + (-)-(1S,4S,9R)-Δ6-trans-Octalin-1,4-diol (3198-50-3) → 1β,4α-bis(benzyloxy)-1,2,3,4,4aβ,5,8,8aα-octahydronaphthalene (84131-75-9)

Guidance literature:

With sodium hydride; In dimethyl sulfoxide; at 25 ℃;

DOI:10.1021/ja00411a063

Reference yield:

(+/-)-1,4,5,8,9,10-trans-hexahydronaphthalene-1,4-dione (2906-93-6,3198-51-4,6102-42-7,36159-09-8,54963-84-7,84275-37-6) → 1β,4α-bis(benzyloxy)-1,2,3,4,4aβ,5,8,8aα-octahydronaphthalene (84131-75-9)

Guidance literature:

Multi-step reaction with 2 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

With Aureobasidium pullulans NRRL Y-12610; sodium hydride; In water; dimethyl sulfoxide;

DOI:10.1021/ja00341a046

Reference yield:

1β,4α-bis(benzyloxy)-1,2,3,4,4aβ,5,8,8aα-octahydronaphthalene (84131-75-9) → mevastatin (73573-88-3,58948-09-7)

Guidance literature:

Multi-step reaction with 20 steps

1: 32 g / acetic acid / 1 h / 25 °C

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

3: 30percent H₂O₂ / tetrahydrofuran; H₂O / 2.5 h / 25 °C

4: tetrahydrofuran; H₂O / 2 h / 55 °C

5: 20.6 g / Jones reagent / tetrahydrofuran; H₂O; acetone / 0.25 h

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

7: 38 g / Et₃N / CH₂Cl₂ / 0.5 h / -5 °C

8: 28.09 g / DBU / benzene / 1 h / 25 °C

9: 78 percent / H₂ / 10percent Pd/C / benzene; pyridine / 0.67 h / 25 °C

10: Et₃N, Na₂SO₄ / ethanol / 7 h / 25 °C

11: 5.3 g / LDA / tetrahydrofuran; hexane / -78 deg C -> 0 deg C, 1 h; 0 deg C, 4 h

12: 100 percent / Li, NH₃ liq. / tetrahydrofuran / 0.5 h

13: 1 mg / 4-(dimethylamino)pyridine / pyridine / 16 h / 25 °C

14: 2.8 g / pyridine / 8 h / 0 °C

15: 1.8 g / DBU / pyridine / 3 h / Heating

16: 1.44 g / acetic acid; tetrahydrofuran; H₂O / 8 h / 25 °C

17: 65 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h / 25 °C

18: 1.) NaH, 2.) n-BuLi / 1.) THF, 0 deg C, 10 min, 2.) THF-hexane, 0 deg C, 10 min, 3.) 0 deg C, 15 min

19: 34 mg / Zn(BH₄)2 / diethyl ether / 1 h / 25 °C

20: 32 mg / p-toluenesulfonic acid monohydrate / benzene / 0.25 h / 25 °C

With dmap; potassium hydroxide; n-butyllithium; jones reagent; zinc(II) tetrahydroborate; ammonia; hydrogen; dihydrogen peroxide; lithium; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium sulfate; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; acetic acid; acetone; benzene;

DOI:10.1021/ja00341a046

upstream raw materials:

benzyl chloride

(-)-(1S,4S,9R)-Δ⁶-trans-Octalin-1,4-diol

(+/-)-1,4,5,8,9,10-trans-hexahydronaphthalene-1,4-dione

Downstream raw materials:

7α-acetoxy-1β,4α-bis(benzyloxy)-6β-(phenylselenyl)-4aβ,8aα-decahydronaphthalene

Acetic acid (2S,4aS,5R,8R,8aS)-5,8-bis-benzyloxy-3-phenylselanyl-decahydro-naphthalen-2-yl ester

mevastatin

(4aS,5R,8R,8aS)-5,8-Bis-benzyloxy-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-ol