(5S,6R,13S,14S,E)-5-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-6,13-dihydroxy-2,2,3,3,14,18,18-heptamethyl-17,17-diphenyl-4,16-dioxa-3,17-disilanonadec-7-en-9-one

Base Information

• Chemical Name: (5S,6R,13S,14S,E)-5-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-6,13-dihydroxy-2,2,3,3,14,18,18-heptamethyl-17,17-diphenyl-4,16-dioxa-3,17-disilanonadec-7-en-9-one
• CAS No.: 1289512-90-8
• Molecular Formula: C₆₀H₉₄O₁₀Si₃
• Molecular Weight: 1059.66
• Mol file: 1289512-90-8.mol

Synonyms:(5S,6R,13S,14S,E)-5-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-6,13-dihydroxy-2,2,3,3,14,18,18-heptamethyl-17,17-diphenyl-4,16-dioxa-3,17-disilanonadec-7-en-9-one

Chemical Property of (5S,6R,13S,14S,E)-5-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-6,13-dihydroxy-2,2,3,3,14,18,18-heptamethyl-17,17-diphenyl-4,16-dioxa-3,17-disilanonadec-7-en-9-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6R,13S,14S,E)-5-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-6,13-dihydroxy-2,2,3,3,14,18,18-heptamethyl-17,17-diphenyl-4,16-dioxa-3,17-disilanonadec-7-en-9-one

There total 5 articles about (5S,6R,13S,14S,E)-5-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-6,13-dihydroxy-2,2,3,3,14,18,18-heptamethyl-17,17-diphenyl-4,16-dioxa-3,17-disilanonadec-7-en-9-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: 52.0%

(7S,8S)-9-[(tert-butyldiphenylsilyl)oxy]-7-hydroxy-8-methylnon-1-en-3-one (1289512-72-6) + (1S,2R)-1-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-1-[(tert-butyldimethylsilyl)oxy]but-3-en-2-ol (1289512-65-7) → (5S,6R,13S,14S,E)-5-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-6,13-dihydroxy-2,2,3,3,14,18,18-heptamethyl-17,17-diphenyl-4,16-dioxa-3,17-disilanonadec-7-en-9-one (1289512-90-8)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 17h; Inert atmosphere; Reflux;

DOI:10.1002/ejoc.201001411

Reference yield:

(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol (1289512-61-3) → (5S,6R,13S,14S,E)-5-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-6,13-dihydroxy-2,2,3,3,14,18,18-heptamethyl-17,17-diphenyl-4,16-dioxa-3,17-disilanonadec-7-en-9-one (1289512-90-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.13 h / -50 - -30 °C / Inert atmosphere

1.2: 0.75 h / -30 °C / Inert atmosphere

1.3: 0.17 h / -30 °C / Inert atmosphere

2.1: tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 17 h / Inert atmosphere; Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation / 1.2: Swern oxidation / 1.3: Swern oxidation;

DOI:10.1002/ejoc.201001411

Reference yield:

(1S,3R,5S)-1-benzyloxymethyl-3-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-5-methyl-2,8-dioxa-bicyclo[3.2.1]octane (1063713-63-2) → (5S,6R,13S,14S,E)-5-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-6,13-dihydroxy-2,2,3,3,14,18,18-heptamethyl-17,17-diphenyl-4,16-dioxa-3,17-disilanonadec-7-en-9-one (1289512-90-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine hydrogenfluoride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.13 h / -50 - -30 °C / Inert atmosphere

2.2: 0.75 h / -30 °C / Inert atmosphere

2.3: 0.17 h / -30 °C / Inert atmosphere

3.1: tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 17 h / Inert atmosphere; Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; oxalyl dichloride; pyridine hydrogenfluoride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation / 2.3: Swern oxidation;

DOI:10.1002/ejoc.201001411

upstream raw materials:

(1S,3R,5S)-1-benzyloxymethyl-3-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-5-methyl-2,8-dioxa-bicyclo[3.2.1]octane

(7S,8S)-9-[(tert-butyldiphenylsilyl)oxy]-7-hydroxy-8-methylnon-1-en-3-one

(1S,2R)-1-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-1-[(tert-butyldimethylsilyl)oxy]but-3-en-2-ol

(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol

Downstream raw materials:

(5S,6R,13S,14S)-5-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-6,13-dihydroxy-2,2,3,3,14,18,18-heptamethyl-17,17-diphenyl-4,16-dioxa-3,17-disilanonadecan-9-one

((S)-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-((2R,5R,7S)-7((S)-1-[(tert-butyldiphenylsilyl)oxy]propan-2-yl)-1,6-dioxaspiro[4.5]decan-2-yl)methoxy)(tert-butyl)dimethylsilane

((S)-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-((2R,5S,7S)-7((S)-1-[(tert-butyldiphenylsilyl)oxy]propan-2-yl)-1,6-dioxaspiro[4.5]decan-2-yl)methoxy)(tert-butyl)dimethylsilane

(2S,3R,6S,8S)-2-((2R,4R,5S)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-hydroxy-2-methyltetrahydrofuran-2-yl)-8-[(S)-1hydroxypropan-2-yl]-1,7-dioxaspiro[5.5]undecan-3-ol