(1S,2R,3R,5R,7R,8S)-8-benzyloxy-2,6,6,7-tetramethyltricyclo<5.2.2.0^1,5>undec-3-yl methanesulfonate

Base Information

• Chemical Name: (1S,2R,3R,5R,7R,8S)-8-benzyloxy-2,6,6,7-tetramethyltricyclo<5.2.2.0^1,5>undec-3-yl methanesulfonate
• CAS No.: 139640-19-0
• Molecular Formula: C₂₃H₃₄O₄S
• Molecular Weight: 406.587

Synonyms:(1S,2R,3R,5R,7R,8S)-8-benzyloxy-2,6,6,7-tetramethyltricyclo<5.2.2.0^1,5>undec-3-yl methanesulfonate

Chemical Property of (1S,2R,3R,5R,7R,8S)-8-benzyloxy-2,6,6,7-tetramethyltricyclo<5.2.2.0^1,5>undec-3-yl methanesulfonate

Chemical Property:

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Technology Process of (1S,2R,3R,5R,7R,8S)-8-benzyloxy-2,6,6,7-tetramethyltricyclo<5.2.2.0^1,5>undec-3-yl methanesulfonate

There total 5 articles about (1S,2R,3R,5R,7R,8S)-8-benzyloxy-2,6,6,7-tetramethyltricyclo<5.2.2.0^1,5>undec-3-yl methanesulfonate 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: 95.0%

methanesulfonyl chloride (124-63-0) + (1S,2R,3R,5R,7R, 8S)-8-benzyloxy-2,6,6,7-tetramethyltricyclo<5.2.2.01,5>undecan-3-ol (139640-18-9) → (1S,2R,3R,5R,7R,8S)-8-benzyloxy-2,6,6,7-tetramethyltricyclo<5.2.2.01,5>undec-3-yl methanesulfonate (139640-19-0)

Guidance literature:

With triethylamine; In dichloromethane; Ambient temperature;

DOI:10.1246/bcsj.65.203

Reference yield:

benzyl bromide (100-39-0) → (1S,2R,3R,5R,7R,8S)-8-benzyloxy-2,6,6,7-tetramethyltricyclo<5.2.2.01,5>undec-3-yl methanesulfonate (139640-19-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / 1.) sodium hydride / 1.) THF, 2 h, reflux, 2.) THF, 15 h, reflux

2: 61 percent / 1.) diborane / tetrahydrofuran / 4 h / Ambient temperature

3: 95 percent / Et₃N / CH₂Cl₂ / Ambient temperature

With sodium hydride; triethylamine; diborane; In tetrahydrofuran; dichloromethane;

DOI:10.1246/bcsj.65.203

Reference yield:

(1S,5R,5R,8S)-8-benzyloxy-2,6,6,7-tetramethyltricyclo<5.2.2.01,5>undec-2-ene (139640-17-8) → (1S,2R,3R,5R,7R,8S)-8-benzyloxy-2,6,6,7-tetramethyltricyclo<5.2.2.01,5>undec-3-yl methanesulfonate (139640-19-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / 1.) diborane / tetrahydrofuran / 4 h / Ambient temperature

2: 95 percent / Et₃N / CH₂Cl₂ / Ambient temperature

With triethylamine; diborane; In tetrahydrofuran; dichloromethane;

DOI:10.1246/bcsj.65.203

upstream raw materials:

methanesulfonyl chloride

(1S,2R,3R,5R,7R, 8S)-8-benzyloxy-2,6,6,7-tetramethyltricyclo<5.2.2.0^1,5>undecan-3-ol

benzyl bromide

(1S,5R,5R,8S)-8-benzyloxy-2,6,6,7-tetramethyltricyclo<5.2.2.0^1,5>undec-2-ene

Downstream raw materials:

(1R,2S,5R,7R)-2,6,6,7-tetramethyltricyclo<5.2.2.0^1,5>undecan-8-one

(3S,3aR,6R,7aR,9S)-9-Benzyloxy-3,6,7,7-tetramethyl-octahydro-3a,6-ethano-indene

(1R,2S,5R,7R,8S)-2,6,6,7-tetramethyltricyclo<5.2.2.0^1,5>undecan-8-ol

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