(4S,5R,6R,9S,10R)-9-(benzoyloxy)-1-hydroxy-5-<(4-methoxybenzyl)oxy>-4,6,10-trimethyl-11-dodecene

Base Information

Chemical Name:(4S,5R,6R,9S,10R)-9-(benzoyloxy)-1-hydroxy-5-<(4-methoxybenzyl)oxy>-4,6,10-trimethyl-11-dodecene
CAS No.:175613-26-0
Molecular Formula:C₃₀H₄₂O₅
Molecular Weight:482.66
Hs Code.:

Synonyms:(4S,5R,6R,9S,10R)-9-(benzoyloxy)-1-hydroxy-5-<(4-methoxybenzyl)oxy>-4,6,10-trimethyl-11-dodecene

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Chemical Property of (4S,5R,6R,9S,10R)-9-(benzoyloxy)-1-hydroxy-5-<(4-methoxybenzyl)oxy>-4,6,10-trimethyl-11-dodecene

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Technology Process of (4S,5R,6R,9S,10R)-9-(benzoyloxy)-1-hydroxy-5-<(4-methoxybenzyl)oxy>-4,6,10-trimethyl-11-dodecene

There total 7 articles about (4S,5R,6R,9S,10R)-9-(benzoyloxy)-1-hydroxy-5-<(4-methoxybenzyl)oxy>-4,6,10-trimethyl-11-dodecene 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%

: 175613-25-9
Benzoic acid (1S,4R,5R,6S)-9-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-4,6-dimethyl-1-((R)-1-methyl-allyl)-nonyl ester

: 175613-26-0
(4S,5R,6R,9S,10R)-9-(benzoyloxy)-1-hydroxy-5-<(4-methoxybenzyl)oxy>-4,6,10-trimethyl-11-dodecene

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2.75h; Ambient temperature;
DOI:10.1021/jo952083l

Reference yield:

: 175613-22-6
(4S,5R,6R)-1-(tert-butyldimethylsiloxy)-5-<(4-methoxybenzyl)oxy>-4,6-dimethyl-9-decene

: 175613-26-0
(4S,5R,6R,9S,10R)-9-(benzoyloxy)-1-hydroxy-5-<(4-methoxybenzyl)oxy>-4,6,10-trimethyl-11-dodecene

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) O₃, 2.) tributylphosphine / 1) CH₂Cl₂, -78 deg C, 5 min; 2) CH₂Cl₂, rt, 2.5 h

2: 1.) potassium tert-butoxide, n-BuLi, (+)-methoxydiisopinocamphenylborane, 2.) BF₃*OEt₂, 3.) aq. H₂O₂

3: 85 percent / DMAP / pyridine / 4.5 h

4: 100 percent / TBAF / tetrahydrofuran / 2.75 h / Ambient temperature

With dmap; n-butyllithium; tributylphosphine; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; ozone; (+)-B-methoxydiisocamphenylborane; In tetrahydrofuran; pyridine;
DOI:10.1021/jo952083l

Reference yield:

: 175613-20-4
(4S,5R,6R)-1-(tert-butyldimethylsiloxy)-4-(hydroxymethyl)-5-<(4-methoxybenzyl)oxy>-6-methyl-9-decene

: 175613-26-0
(4S,5R,6R,9S,10R)-9-(benzoyloxy)-1-hydroxy-5-<(4-methoxybenzyl)oxy>-4,6,10-trimethyl-11-dodecene

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / Et₃N / toluene; CH₂Cl₂ / 0.5 h / 0 °C

2: 88 percent / LiAlH₄ / toluene; tetrahydrofuran / 1) rt, 10 min; 2) 60 deg C, 13 min

3: 1.) O₃, 2.) tributylphosphine / 1) CH₂Cl₂, -78 deg C, 5 min; 2) CH₂Cl₂, rt, 2.5 h

4: 1.) potassium tert-butoxide, n-BuLi, (+)-methoxydiisopinocamphenylborane, 2.) BF₃*OEt₂, 3.) aq. H₂O₂

5: 85 percent / DMAP / pyridine / 4.5 h

6: 100 percent / TBAF / tetrahydrofuran / 2.75 h / Ambient temperature

With dmap; lithium aluminium tetrahydride; n-butyllithium; tributylphosphine; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; ozone; triethylamine; (+)-B-methoxydiisocamphenylborane; In tetrahydrofuran; pyridine; dichloromethane; toluene;
DOI:10.1021/jo952083l