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

Base Information

• Chemical Name: (1S,2R,3R,5R,7R, 8S)-8-benzyloxy-2,6,6,7-tetramethyltricyclo<5.2.2.0^1,5>undecan-3-ol
• CAS No.: 139640-18-9
• Molecular Formula: C₂₂H₃₂O₂
• Molecular Weight: 328.495

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

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

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>undecan-3-ol

There total 4 articles about (1S,2R,3R,5R,7R, 8S)-8-benzyloxy-2,6,6,7-tetramethyltricyclo<5.2.2.0^1,5>undecan-3-ol 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: 61.0%

(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>undecan-3-ol (139640-18-9)

Guidance literature:

With diborane; In tetrahydrofuran; for 4h; 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>undecan-3-ol (139640-18-9)

Guidance literature:

Multi-step reaction with 2 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

With sodium hydride; diborane; In tetrahydrofuran;

DOI:10.1246/bcsj.65.203

Reference yield:

Formic acid (3aR,6S,7aR)-3,6,7,7-tetramethyl-1,4,5,6,7,7a-hexahydro-3a,6-ethano-inden-9-yl ester (139640-14-5,139686-88-7) → (1S,2R,3R,5R,7R, 8S)-8-benzyloxy-2,6,6,7-tetramethyltricyclo<5.2.2.01,5>undecan-3-ol (139640-18-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 284 mg / 5percent KOH in methanol / 12 h / Ambient temperature

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

3: 61 percent / 1.) diborane / tetrahydrofuran / 4 h / Ambient temperature

With potassium hydroxide; sodium hydride; diborane; In tetrahydrofuran;

DOI:10.1246/bcsj.65.203

upstream raw materials:

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

benzyl bromide

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

Formic acid (3aR,6S,7aR)-3,6,7,7-tetramethyl-1,4,5,6,7,7a-hexahydro-3a,6-ethano-inden-9-yl ester

Downstream raw materials:

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

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

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

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

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