Silane, [[(1R,2R,3R,6R)-4-methylene-3,6-bis(phenylmethoxy)-1,2-cyclohexane diyl]bis(oxy)]bis[(1,1-dimethylethyl)dimethyl-

Base Information

• Chemical Name: Silane, [[(1R,2R,3R,6R)-4-methylene-3,6-bis(phenylmethoxy)-1,2-cyclohexane diyl]bis(oxy)]bis[(1,1-dimethylethyl)dimethyl-
• CAS No.: 274692-85-2
• Molecular Formula: C33H52O4Si2
• Molecular Weight: 568.944
• Mol file: 274692-85-2.mol

Synonyms:

Chemical Property of Silane, [[(1R,2R,3R,6R)-4-methylene-3,6-bis(phenylmethoxy)-1,2-cyclohexane diyl]bis(oxy)]bis[(1,1-dimethylethyl)dimethyl-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Silane, [[(1R,2R,3R,6R)-4-methylene-3,6-bis(phenylmethoxy)-1,2-cyclohexane diyl]bis(oxy)]bis[(1,1-dimethylethyl)dimethyl-

There total 6 articles about Silane, [[(1R,2R,3R,6R)-4-methylene-3,6-bis(phenylmethoxy)-1,2-cyclohexane diyl]bis(oxy)]bis[(1,1-dimethylethyl)dimethyl- 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: 89.0%

t-butyldimethylsiyl triflate (69739-34-0) + (1R,2R,3R,4R)-1,4-di-benzyloxy-5-methylenecyclohexane-2,3-diol (274692-80-7) → (1R,2R,3R,4R)-1,4-di-benzyloxy-2,3-(tert-butyldimethyl)silyloxy-5-methylenecyclohexane (274692-85-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.0833333h;

DOI:10.1002/1099-0690(200004)2000:7<1285::AID-EJOC1285>3.0.CO;2-Z

Reference yield:

D-1,6-O-(1-methylethylidene)-2,5-bis-O-(phenylmethyl)-allo-inositol (188839-35-2,173828-64-3) → (1R,2R,3R,4R)-1,4-di-benzyloxy-2,3-(tert-butyldimethyl)silyloxy-5-methylenecyclohexane (274692-85-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: thionyl chloride; triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

2.1: 99 mg / NaIO₄; ruthenium trichloride / CCl₄; acetonitrile; H₂O / 1 h / 0 °C

3.1: tBuOK / tetrahydrofuran / 1.5 h / 20 °C

3.2: 86 percent / H₂SO₄ / tetrahydrofuran; H₂O / 0.5 h / 20 °C

4.1: 85 percent / KHMDS / tetrahydrofuran / 30 h / 5 °C

5.1: 98 percent / CF₃COOH / methanol / 0.5 h / 20 °C

6.1: 89 percent / iPr₂EtN / CH₂Cl₂ / 0.08 h / 20 °C

With ruthenium trichloride; sodium periodate; thionyl chloride; potassium tert-butylate; potassium hexamethylsilazane; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; acetonitrile; 1.1: Condensation / 2.1: Oxidation / 3.1: Ring cleavage / 3.2: Elimination / 4.1: Wittig olefination / 5.1: Hydrolysis / 6.1: Substitution;

DOI:10.1002/1099-0690(200004)2000:7<1285::AID-EJOC1285>3.0.CO;2-Z

Reference yield:

(2R,3R,4R,5R)-2,5-di-benzyloxy-3,4-(isopropylidenedioxy)cyclohexan-1-one (274692-78-3) → (1R,2R,3R,4R)-1,4-di-benzyloxy-2,3-(tert-butyldimethyl)silyloxy-5-methylenecyclohexane (274692-85-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / KHMDS / tetrahydrofuran / 30 h / 5 °C

2: 98 percent / CF₃COOH / methanol / 0.5 h / 20 °C

3: 89 percent / iPr₂EtN / CH₂Cl₂ / 0.08 h / 20 °C

With potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; 1: Wittig olefination / 2: Hydrolysis / 3: Substitution;

DOI:10.1002/1099-0690(200004)2000:7<1285::AID-EJOC1285>3.0.CO;2-Z

upstream raw materials:

t-butyldimethylsiyl triflate

(1R,2R,3R,4R)-1,4-di-benzyloxy-5-methylenecyclohexane-2,3-diol

D-1,6-O-(1-methylethylidene)-2,5-bis-O-(phenylmethyl)-allo-inositol

(2R,3R,4R,5R)-2,5-di-benzyloxy-3,4-(isopropylidenedioxy)cyclohexan-1-one

Downstream raw materials:

1L-(1,2,3/4,5)-1-C-Methyl-2,3,4,5-cyclohexanetetrol

4-O-benzyl-5a-carba-α-L-fucopyranose

2,3-(tert-butyldimethyl)silyloxy-5a-carba-α-L-fucopyranose

4-O-benzyl-2,3-di-O-(tert-butyldimethyl)silyl-5a-carba-α-L-fucopyranose