((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

Base Information

• Chemical Name: ((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
• CAS No.: 1289512-96-4
• Molecular Formula: C₆₀H₉₄O₉Si₃
• Molecular Weight: 1043.66
• Mol file: 1289512-96-4.mol

Synonyms:

Chemical Property of ((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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((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

There total 8 articles about ((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 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:

(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 (1289512-95-3) → ((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 (1289512-96-4) + ((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 (1289512-98-6)

Guidance literature:

With chloroacetic acid; In dichloromethane; at 20 ℃; for 1h; optical yield given as %de; Inert atmosphere;

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) → ((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 (1289512-96-4)

Guidance literature:

Multi-step reaction with 6 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

5.1: pyridine; 5% Pd(II)/C(eggshell); hydrogen / ethyl acetate / 4 h / Inert atmosphere

6.1: chloroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

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

DOI:10.1002/ejoc.201001411

Reference yield:

(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) → ((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 (1289512-96-4)

Guidance literature:

Multi-step reaction with 3 steps

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

2: pyridine; 5% Pd(II)/C(eggshell); hydrogen / ethyl acetate / 4 h / Inert atmosphere

3: chloroacetic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 5% Pd(II)/C(eggshell); hydrogen; chloroacetic acid; In dichloromethane; ethyl acetate;

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

(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

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

(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

Downstream raw materials:

((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

(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