Triisopropyl-[(Z)-(1R,4S,5R,9R,11S,12S)-5-isopropyl-1-methoxy-11-(4-methoxy-benzyloxy)-8,12-dimethyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-2,7,13-trien-2-ylmethoxy]-silane

Base Information

• Chemical Name: Triisopropyl-[(Z)-(1R,4S,5R,9R,11S,12S)-5-isopropyl-1-methoxy-11-(4-methoxy-benzyloxy)-8,12-dimethyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-2,7,13-trien-2-ylmethoxy]-silane
• CAS No.: 198336-13-9
• Molecular Formula: C₃₈H₆₀O₅Si
• Molecular Weight: 624.977

Synonyms:Triisopropyl-[(Z)-(1R,4S,5R,9R,11S,12S)-5-isopropyl-1-methoxy-11-(4-methoxy-benzyloxy)-8,12-dimethyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-2,7,13-trien-2-ylmethoxy]-silane

Chemical Property of Triisopropyl-[(Z)-(1R,4S,5R,9R,11S,12S)-5-isopropyl-1-methoxy-11-(4-methoxy-benzyloxy)-8,12-dimethyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-2,7,13-trien-2-ylmethoxy]-silane

Chemical Property:

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Technology Process of Triisopropyl-[(Z)-(1R,4S,5R,9R,11S,12S)-5-isopropyl-1-methoxy-11-(4-methoxy-benzyloxy)-8,12-dimethyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-2,7,13-trien-2-ylmethoxy]-silane

There total 29 articles about Triisopropyl-[(Z)-(1R,4S,5R,9R,11S,12S)-5-isopropyl-1-methoxy-11-(4-methoxy-benzyloxy)-8,12-dimethyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-2,7,13-trien-2-ylmethoxy]-silane 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: 100.0%

methanol (67-56-1) + (Z)-(1R,4S,5R,9R,11S,12S)-5-Isopropyl-11-(4-methoxy-benzyloxy)-8,12-dimethyl-2-triisopropylsilanyloxymethyl-15-oxa-tricyclo[10.2.1.04,9]pentadeca-2,7,13-trien-1-ol (198336-12-8) → Triisopropyl-[(Z)-(1R,4S,5R,9R,11S,12S)-5-isopropyl-1-methoxy-11-(4-methoxy-benzyloxy)-8,12-dimethyl-15-oxa-tricyclo[10.2.1.04,9]pentadeca-2,7,13-trien-2-ylmethoxy]-silane (198336-13-9)

Guidance literature:

With pyridinium p-toluenesulfonate; at 25 ℃; for 0.166667h;

DOI:10.1021/ja981062g

Reference yield:

(1R,2R,6R)-2-[(2S,3S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-3-methyl-pent-4-ynyl]-6-isopropyl-3-methyl-cyclohex-3-enecarbaldehyde (223762-75-2) → Triisopropyl-[(Z)-(1R,4S,5R,9R,11S,12S)-5-isopropyl-1-methoxy-11-(4-methoxy-benzyloxy)-8,12-dimethyl-15-oxa-tricyclo[10.2.1.04,9]pentadeca-2,7,13-trien-2-ylmethoxy]-silane (198336-13-9)

Guidance literature:

Multi-step reaction with 9 steps

1: β-alanine / aq. ethanol / 72 h / 25 °C

2: (iPr)2NEt / CH₂Cl₂ / 2 h / -78 °C

3: 80 percent / DIBAL / hexane; tetrahydrofuran / 5 h / -78 - -40 °C

4: 91 percent / iPr₂NEt / CH₂Cl₂ / 1 h / -78 °C

5: LiHMDS / tetrahydrofuran / 0.17 h / 25 °C

6: NaHCO₃, Dess-Martin periodinane / CH₂Cl₂ / 4 h / 25 °C

7: 94 percent / PPTS / methanol / 0.5 h / 25 °C

8: 75 percent / H₂ / Lindlar cat. / toluene / 0.33 h / 25 °C / 760 Torr

9: 100 percent / PPTS / 0.17 h / 25 °C

With hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; 3-amino propanoic acid; Lindlar catalyst; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; toluene;

DOI:10.1021/ja981062g

Reference yield:

(Z)-2-Hydroxymethyl-3-{(1S,2R,6R)-6-isopropyl-2-[(2S,3S)-2-(4-methoxy-benzyloxy)-3-methyl-3-trimethylsilanyloxy-pent-4-ynyl]-3-methyl-cyclohex-3-enyl}-propenal (198336-08-2) → Triisopropyl-[(Z)-(1R,4S,5R,9R,11S,12S)-5-isopropyl-1-methoxy-11-(4-methoxy-benzyloxy)-8,12-dimethyl-15-oxa-tricyclo[10.2.1.04,9]pentadeca-2,7,13-trien-2-ylmethoxy]-silane (198336-13-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / iPr₂NEt / CH₂Cl₂ / 1 h / -78 °C

2: LiHMDS / tetrahydrofuran / 0.17 h / 25 °C

3: NaHCO₃, Dess-Martin periodinane / CH₂Cl₂ / 4 h / 25 °C

4: 94 percent / PPTS / methanol / 0.5 h / 25 °C

5: 75 percent / H₂ / Lindlar cat. / toluene / 0.33 h / 25 °C / 760 Torr

6: 100 percent / PPTS / 0.17 h / 25 °C

With hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; Lindlar catalyst; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/ja981062g

upstream raw materials:

methanol

(Z)-(1R,4S,5R,9R,11S,12S)-5-Isopropyl-11-(4-methoxy-benzyloxy)-8,12-dimethyl-2-triisopropylsilanyloxymethyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-2,7,13-trien-1-ol

(1S,4S,6S)-4-Isopropyl-1-methyl-7-oxa-bicyclo[4.1.0]heptan-2-one

(S)-p-mentha-6,8-dien-2-one

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