(4S,5R,6R)-1-(tert-butyldimethylsiloxy)-4-<(methanesulfonyl)methyl>-5-<(4-methoxybenzyl)oxy>-6-methyl-9-decene

Base Information

Chemical Name:(4S,5R,6R)-1-(tert-butyldimethylsiloxy)-4-<(methanesulfonyl)methyl>-5-<(4-methoxybenzyl)oxy>-6-methyl-9-decene
CAS No.:175613-21-5
Molecular Formula:C₂₇H₄₈O₆SSi
Molecular Weight:528.826
Hs Code.:

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

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Chemical Property of (4S,5R,6R)-1-(tert-butyldimethylsiloxy)-4-<(methanesulfonyl)methyl>-5-<(4-methoxybenzyl)oxy>-6-methyl-9-decene

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Technology Process of (4S,5R,6R)-1-(tert-butyldimethylsiloxy)-4-<(methanesulfonyl)methyl>-5-<(4-methoxybenzyl)oxy>-6-methyl-9-decene

There total 1 articles about (4S,5R,6R)-1-(tert-butyldimethylsiloxy)-4-<(methanesulfonyl)methyl>-5-<(4-methoxybenzyl)oxy>-6-methyl-9-decene 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:

: (1S,2S,6R,8S)-4-[(2S,3S,4R)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-3-(4-methoxy-benzyloxy)-4-methyl-oct-7-enyl]-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0^2,6]decane

: 175613-21-5
(4S,5R,6R)-1-(tert-butyldimethylsiloxy)-4-<(methanesulfonyl)methyl>-5-<(4-methoxybenzyl)oxy>-6-methyl-9-decene

Guidance literature:: Multi-step reaction with 2 steps

1: aq. H₂O₂, NaOH / 1 h / Ambient temperature

2: 94 percent / Et₃N / toluene; CH₂Cl₂ / 0.5 h / 0 °C

With sodium hydroxide; dihydrogen peroxide; triethylamine; In dichloromethane; toluene;
DOI:10.1021/jo952083l

Reference yield: 88.0%

: 175613-21-5
(4S,5R,6R)-1-(tert-butyldimethylsiloxy)-4-<(methanesulfonyl)methyl>-5-<(4-methoxybenzyl)oxy>-6-methyl-9-decene

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

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; toluene; 1) rt, 10 min; 2) 60 deg C, 13 min;
DOI:10.1021/jo952083l

Reference yield:

: 175613-21-5
(4S,5R,6R)-1-(tert-butyldimethylsiloxy)-4-<(methanesulfonyl)methyl>-5-<(4-methoxybenzyl)oxy>-6-methyl-9-decene

: Benzoic acid (1S,4R,5S,6S,12R,13S,16S,17R)-17-(tert-butyl-diphenyl-silanyloxy)-5,13-bis-(4-methoxy-benzyloxy)-4,6,12,16-tetramethyl-1-((R)-1-methyl-allyl)-9-oxo-octadecyl ester

Guidance literature:: Multi-step reaction with 9 steps

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

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

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

4: 85 percent / DMAP / pyridine / 4.5 h

5: 100 percent / TBAF / tetrahydrofuran / 2.75 h / Ambient temperature

6: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -78 deg C, 1 h; 2) CH₂Cl₂, -78 deg C, 20 min

7: 65 percent / CrCl₂, NiCl₂ / toluene; tetrahydrofuran; dimethylformamide / 60 h

8: 96 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / 1 h / Ambient temperature

9: 99.7 percent / (PPh₃CuH)6 / benzene-d6 / 1 h

With pyridine; chromium dichloride; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; tributylphosphine; (PPh₃CuH)6; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; Dess-Martin periodane; ozone; dimethyl sulfoxide; triethylamine; (+)-B-methoxydiisocamphenylborane; nickel dichloride; In tetrahydrofuran; pyridine; dichloromethane; benzene-d6; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo952083l