(2R,4R,6R,7S,8R,9R)-2-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-one

Base Information

• Chemical Name: (2R,4R,6R,7S,8R,9R)-2-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-one
• CAS No.: 114114-27-1
• Molecular Formula: C₃₈H₆₆O₆Si
• Molecular Weight: 647.024
• Mol file: 114114-27-1.mol

Synonyms:(2R,4R,6R,7S,8R,9R)-2-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-one

Chemical Property of (2R,4R,6R,7S,8R,9R)-2-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R,6R,7S,8R,9R)-2-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-one

There total 11 articles about (2R,4R,6R,7S,8R,9R)-2-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-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: 65.0%

(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal (114181-55-4) + (4R,6R)-6-Benzyloxy-4-methyl-6-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-heptan-3-one (114114-23-7) → (2R,4R,6R,7S,8R,9R)-2-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-one (114114-27-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)96400-1

Reference yield:

(2S,3S,4R)-1,1-Bis-ethylsulfanyl-3-methyl-hexane-2,4-diol → (2R,4R,6R,7S,8R,9R)-2-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-one (114114-27-1)

Guidance literature:

Multi-step reaction with 6 steps

1: Ra-Ni / ethanol

2: CuSO₄

3: Et₃N / CH₂Cl₂

4: HS(CH₂)SH, BF₃*Et₂O / CH₂Cl₂ / -78 °C

5: NaIO₄ / tetrahydrofuran; H₂O

6: 65 percent / LiN(SiMe₃)2 / tetrahydrofuran / -78 °C

With sodium periodate; 1,3-dithiapropane; boron trifluoride diethyl etherate; copper(II) sulfate; triethylamine; lithium hexamethyldisilazane; Ra-Ni; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1016/S0040-4039(00)96400-1

Reference yield:

(1S,2S,3S,5R)-2-methyl-6,8-dioxabicyclo<3.2.1>octan-3-ol (85433-13-2) → (2R,4R,6R,7S,8R,9R)-2-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-7-hydroxy-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecan-5-one (114114-27-1)

Guidance literature:

Multi-step reaction with 7 steps

1: HCl

2: Ra-Ni / ethanol

3: CuSO₄

4: Et₃N / CH₂Cl₂

5: HS(CH₂)SH, BF₃*Et₂O / CH₂Cl₂ / -78 °C

6: NaIO₄ / tetrahydrofuran; H₂O

7: 65 percent / LiN(SiMe₃)2 / tetrahydrofuran / -78 °C

With hydrogenchloride; sodium periodate; 1,3-dithiapropane; boron trifluoride diethyl etherate; copper(II) sulfate; triethylamine; lithium hexamethyldisilazane; Ra-Ni; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1016/S0040-4039(00)96400-1

upstream raw materials:

(2S,3R)-3-(tert-butyldimethylsilyloxy)-2-methylpentanal

(4R,6R)-6-Benzyloxy-4-methyl-6-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-heptan-3-one

t-butyldimethylsiyl triflate

1,2,4-tridesoxy-4-C-methyl-5,6-O-isopropylidene-D-arabinohexitol

Downstream raw materials:

(2R,4R,5R,6S,7R,8R,9R)-2-Benzyloxy-9-(tert-butyl-dimethyl-silanyloxy)-4,6,8-trimethyl-2-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-undecane-5,7-diol

{(1R,2R)-2-[(4R,5S,6R)-6-{(1R,3R)-3-Benzyloxy-1-methyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-butyl}-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-1-ethyl-propoxy}-tert-butyl-dimethyl-silane

tert-Butyl-((1R,2R)-1-ethyl-2-{(3R,5R,6S,7S,8R)-1-(4-methoxy-phenyl)-3,5,7-trimethyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-2,9,10-trioxa-bicyclo[4.3.1]dec-8-yl}-propoxy)-dimethyl-silane

{(1R,2R)-2-[(2R,4R,5S,6R)-6-{(1R,3R)-3-Benzyloxy-1-methyl-3-[(4R,5S,6R)-2,2,5-trimethyl-6-((S)-1-methyl-allyl)-[1,3]dioxan-4-yl]-butyl}-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-1-ethyl-propoxy}-tert-butyl-dimethyl-silane