(1R,2R,6S,7S,8S,9R)-9-Benzyloxy-6-hydroxy-2,7,14-trimethyl-tricyclo[5.4.3.0^1,8]tetradecan-4-one

Base Information

• Chemical Name: (1R,2R,6S,7S,8S,9R)-9-Benzyloxy-6-hydroxy-2,7,14-trimethyl-tricyclo[5.4.3.0^1,8]tetradecan-4-one
• CAS No.: 123331-23-7
• Molecular Formula: C₂₄H₃₄O₃
• Molecular Weight: 370.532

Synonyms:(1R,2R,6S,7S,8S,9R)-9-Benzyloxy-6-hydroxy-2,7,14-trimethyl-tricyclo[5.4.3.0^1,8]tetradecan-4-one

Chemical Property of (1R,2R,6S,7S,8S,9R)-9-Benzyloxy-6-hydroxy-2,7,14-trimethyl-tricyclo[5.4.3.0^1,8]tetradecan-4-one

Chemical Property:

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Technology Process of (1R,2R,6S,7S,8S,9R)-9-Benzyloxy-6-hydroxy-2,7,14-trimethyl-tricyclo[5.4.3.0^1,8]tetradecan-4-one

There total 14 articles about (1R,2R,6S,7S,8S,9R)-9-Benzyloxy-6-hydroxy-2,7,14-trimethyl-tricyclo[5.4.3.0^1,8]tetradecan-4-one 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: 67.0%

C26H36O3 (123331-22-6) → (1R,2R,6S,7S,8S,9R)-9-Benzyloxy-6-hydroxy-2,7,14-trimethyl-tricyclo[5.4.3.01,8]tetradecan-4-one (123331-23-7)

Guidance literature:

With toluene-4-sulfonic acid; In water; acetone; for 8h; Heating;

DOI:10.1021/ja00203a043

Reference yield:

5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methyl-cyclohex-2-enone → (1R,2R,6S,7S,8S,9R)-9-Benzyloxy-6-hydroxy-2,7,14-trimethyl-tricyclo[5.4.3.01,8]tetradecan-4-one (123331-23-7)

Guidance literature:

Multi-step reaction with 13 steps

1: LDA / tetrahydrofuran / 2.25 h / -23 °C

2: 1.) pyrrolidine, 2.) AcOH, AcONa / 1.) benzene, reflux, 48 h, 2.) H₂O, reflux, 2h

3: 1.) CH₃COOH, 2.) pyridine / 2.) DMAP / 1.) H₂O, THF, 25 deg C, 8 h, 2.) CH₂Cl₂, 25 deg C, 40 h

4: 1.) Et₂O, -78 deg C, 1.33 h, 2.) HMPA, 0 deg C, 1 h

5: tetrahydrofuran / 0.5 h / 25 °C

6: KH, 18-crown-6 / bis-(2-methoxy-ethyl) ether / 1.5 h / 25 - 115 °C

7: MCPBA / hexane / 12 h / 0 - 25 °C

8: 1) BF₃*Et₂O / 1.) benzene, 25 deg C, 10 min., 2.) 25 deg C, 15 min

9: Li, anhydrous liquid NH₃ / tetrahydrofuran / 1 h / -33 °C

10: 1.) KH / 1.) THF, 0 to 25 deg C, 1 h, 2.) 25 deg C, 20 min

11: PyH⁽¹⁺⁾*Br₃^(1-) / tetrahydrofuran / 10 h / 0 °C

12: t-BuOK / dimethylsulfoxide / 1 h / 110 °C

13: 67 percent / 1 M aq. p-TsOH / H₂O; acetone / 8 h / Heating

With pyrrolidine; pyridine; 18-crown-6 ether; boron trifluoride diethyl etherate; potassium tert-butylate; ammonia; sodium acetate; lithium; potassium hydride; toluene-4-sulfonic acid; acetic acid; pyridinium hydrobromide perbromide; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; dmap; In tetrahydrofuran; hexane; diethylene glycol dimethyl ether; water; dimethyl sulfoxide; acetone;

DOI:10.1021/ja00203a043

Reference yield:

(4R,4aR)-4a-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4,8-dimethyl-4,4a,5,6-tetrahydro-3H-naphthalen-2-one (123331-14-6) → (1R,2R,6S,7S,8S,9R)-9-Benzyloxy-6-hydroxy-2,7,14-trimethyl-tricyclo[5.4.3.01,8]tetradecan-4-one (123331-23-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) CH₃COOH, 2.) pyridine / 2.) DMAP / 1.) H₂O, THF, 25 deg C, 8 h, 2.) CH₂Cl₂, 25 deg C, 40 h

2: 1.) Et₂O, -78 deg C, 1.33 h, 2.) HMPA, 0 deg C, 1 h

3: tetrahydrofuran / 0.5 h / 25 °C

4: KH, 18-crown-6 / bis-(2-methoxy-ethyl) ether / 1.5 h / 25 - 115 °C

5: MCPBA / hexane / 12 h / 0 - 25 °C

6: 1) BF₃*Et₂O / 1.) benzene, 25 deg C, 10 min., 2.) 25 deg C, 15 min

7: Li, anhydrous liquid NH₃ / tetrahydrofuran / 1 h / -33 °C

8: 1.) KH / 1.) THF, 0 to 25 deg C, 1 h, 2.) 25 deg C, 20 min

9: PyH⁽¹⁺⁾*Br₃^(1-) / tetrahydrofuran / 10 h / 0 °C

10: t-BuOK / dimethylsulfoxide / 1 h / 110 °C

11: 67 percent / 1 M aq. p-TsOH / H₂O; acetone / 8 h / Heating

With pyridine; 18-crown-6 ether; boron trifluoride diethyl etherate; potassium tert-butylate; ammonia; lithium; potassium hydride; toluene-4-sulfonic acid; acetic acid; pyridinium hydrobromide perbromide; 3-chloro-benzenecarboperoxoic acid; dmap; In tetrahydrofuran; hexane; diethylene glycol dimethyl ether; water; dimethyl sulfoxide; acetone;

DOI:10.1021/ja00203a043

upstream raw materials:

C₂₆H₃₆O₃

(1R,4R,4aR,7S)-4,7,8-Trimethyl-1,3,4,5,6,7-hexahydro-1,4a-ethano-naphthalen-2-one

(1R,2S,7R)-2,7,14-Trimethyl-tricyclo[5.4.3.0^1,8]tetradec-8-en-4-one

C₁₉H₃₀O₃

Downstream raw materials:

(1R,2S,3R,6S,7S,8S,9R)-9-Benzyloxy-3-hydroxy-6-methoxymethoxy-2,7,14-trimethyl-tricyclo[5.4.3.0^1,8]tetradecan-4-one

(1S,2S,3R,6S,7S,8S,9R)-9-Benzyloxy-3,6-bis-methoxymethoxy-2,7,14-trimethyl-tricyclo[5.4.3.0^1,8]tetradecan-4-one

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