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

Base Information

• Chemical Name: Methanesulfonic acid (1R,4aR,5S,8S,8aR)-5,8-bis-benzyloxy-1-[3-(1-ethoxy-ethoxy)-propyl]-3-oxo-decahydro-naphthalen-2-ylmethyl ester
• CAS No.: 79782-44-8
• Molecular Formula: C₃₃H₄₆O₈S
• Molecular Weight: 602.789
• Mol file: 79782-44-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 20 articles about Methanesulfonic acid (1R,4aR,5S,8S,8aR)-5,8-bis-benzyloxy-1-[3-(1-ethoxy-ethoxy)-propyl]-3-oxo-decahydro-naphthalen-2-ylmethyl ester 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:

methanesulfonyl chloride (124-63-0) + (4aα,8aβ)-5β,8α-bis(benzyloxy)-2(hydroxymethyl)-3-oxo-1β-<3-(1-ethoxyethoxy)propyl>decahydronaphthalene (79782-43-7) → Methanesulfonic acid (1R,4aR,5S,8S,8aR)-5,8-bis-benzyloxy-1-[3-(1-ethoxy-ethoxy)-propyl]-3-oxo-decahydro-naphthalen-2-ylmethyl ester (79782-44-8)

Guidance literature:

With triethylamine; In dichloromethane; at -5 ℃; for 0.5h;

DOI:10.1021/ja00341a046

Reference yield:

methanesulfonyl chloride (124-63-0) + (4R,4aR,5S,8S,8aR)-5,8-Bis-benzyloxy-4-[3-(1-ethoxy-ethoxy)-propyl]-3-hydroxymethyl-octahydro-naphthalen-2-one (79782-43-7) → Methanesulfonic acid (1R,4aR,5S,8S,8aR)-5,8-bis-benzyloxy-1-[3-(1-ethoxy-ethoxy)-propyl]-3-oxo-decahydro-naphthalen-2-ylmethyl ester (79782-44-8)

Guidance literature:

With triethylamine; In dichloromethane; at -5 ℃; for 0.5h;

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

Guidance literature:

Multi-step reaction with 9 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

With potassium hydroxide; jones reagent; Aureobasidium pullulans NRRL Y-12610; dihydrogen peroxide; sodium hydride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; dimethyl sulfoxide; acetone;

DOI:10.1021/ja00341a046

upstream raw materials:

methanesulfonyl chloride

(4aα,8aβ)-5β,8α-bis(benzyloxy)-2(hydroxymethyl)-3-oxo-1β-<3-(1-ethoxyethoxy)propyl>decahydronaphthalene

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

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

Downstream raw materials:

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

mevastatin

3-epi-compactin

3,5-bis-epi-compactin