(1SR,2SR,5RS,6RS,7RS,11SR)-2-hydroxy-5-methoxymethoxy-6,9,9-trimethyl-11-p-toluenesulfonyloxytricyclo<5,4,0,0^2,6>undecan-8-one ethylene acetal

Base Information

• Chemical Name: (1SR,2SR,5RS,6RS,7RS,11SR)-2-hydroxy-5-methoxymethoxy-6,9,9-trimethyl-11-p-toluenesulfonyloxytricyclo<5,4,0,0^2,6>undecan-8-one ethylene acetal
• CAS No.: 72008-72-1
• Molecular Formula: C₂₅H₃₆O₈S
• Molecular Weight: 496.622

Synonyms:(1SR,2SR,5RS,6RS,7RS,11SR)-2-hydroxy-5-methoxymethoxy-6,9,9-trimethyl-11-p-toluenesulfonyloxytricyclo<5,4,0,0^2,6>undecan-8-one ethylene acetal

Chemical Property of (1SR,2SR,5RS,6RS,7RS,11SR)-2-hydroxy-5-methoxymethoxy-6,9,9-trimethyl-11-p-toluenesulfonyloxytricyclo<5,4,0,0^2,6>undecan-8-one ethylene acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1SR,2SR,5RS,6RS,7RS,11SR)-2-hydroxy-5-methoxymethoxy-6,9,9-trimethyl-11-p-toluenesulfonyloxytricyclo<5,4,0,0^2,6>undecan-8-one ethylene acetal

There total 6 articles about (1SR,2SR,5RS,6RS,7RS,11SR)-2-hydroxy-5-methoxymethoxy-6,9,9-trimethyl-11-p-toluenesulfonyloxytricyclo<5,4,0,0^2,6>undecan-8-one ethylene acetal 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:

(1SR,2SR,5RS,6RS,7RS,11SR)-2,11-dihydroxy-5-methoxymethoxy-6,9,9-trimethyltricyclo<5,4,0,02,6>undecan-8-one ethylene acetal (72008-71-0) + p-toluenesulfonyl chloride (98-59-9) → (1SR,2SR,5RS,6RS,7RS,11SR)-2-hydroxy-5-methoxymethoxy-6,9,9-trimethyl-11-p-toluenesulfonyloxytricyclo<5,4,0,02,6>undecan-8-one ethylene acetal (72008-72-1)

Guidance literature:

In pyridine; Yield given; 5 deg C, 1 h, then 19 deg C, 3 h;

DOI:10.1016/0040-4020(81)80002-6

Reference yield:

4-acetoxy-6,6-dimethylcyclohex-2-enone ethylene acetal (72008-65-2) → (1SR,2SR,5RS,6RS,7RS,11SR)-2-hydroxy-5-methoxymethoxy-6,9,9-trimethyl-11-p-toluenesulfonyloxytricyclo<5,4,0,02,6>undecan-8-one ethylene acetal (72008-72-1)

Guidance literature:

Multi-step reaction with 5 steps

1: cyclohexane / 60 h / Irradiation

2: NaBH₄ / methanol / 0.75 h

3: N,N-diisopropylethylamine / CHCl₃ / 5 h / Ambient temperature

4: MeONa / methanol / Ambient temperature

5: pyridine / 5 deg C, 1 h, then 19 deg C, 3 h

With sodium tetrahydroborate; sodium methylate; N-ethyl-N,N-diisopropylamine; In pyridine; methanol; chloroform; cyclohexane;

DOI:10.1016/0040-4020(81)80002-6

Reference yield:

3-acetoxy-2-methylcyclopent-2-en-1-one (3883-57-6) → (1SR,2SR,5RS,6RS,7RS,11SR)-2-hydroxy-5-methoxymethoxy-6,9,9-trimethyl-11-p-toluenesulfonyloxytricyclo<5,4,0,02,6>undecan-8-one ethylene acetal (72008-72-1)

Guidance literature:

Multi-step reaction with 5 steps

1: cyclohexane / 60 h / Irradiation

2: NaBH₄ / methanol / 0.75 h

3: N,N-diisopropylethylamine / CHCl₃ / 5 h / Ambient temperature

4: MeONa / methanol / Ambient temperature

5: pyridine / 5 deg C, 1 h, then 19 deg C, 3 h

With sodium tetrahydroborate; sodium methylate; N-ethyl-N,N-diisopropylamine; In pyridine; methanol; chloroform; cyclohexane;

DOI:10.1016/0040-4020(81)80002-6

upstream raw materials:

(1SR,2SR,5RS,6RS,7RS,11SR)-2,11-dihydroxy-5-methoxymethoxy-6,9,9-trimethyltricyclo<5,4,0,0^2,6>undecan-8-one ethylene acetal

p-toluenesulfonyl chloride

4-acetoxy-6,6-dimethylcyclohex-2-enone ethylene acetal

3-acetoxy-2-methylcyclopent-2-en-1-one

Downstream raw materials:

(+/-)-coriolin

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