(3R,3aR,6S,6aS)-6-[tert-butyl(dimethyl)silyl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol

Base Information

• Chemical Name: (3R,3aR,6S,6aS)-6-[tert-butyl(dimethyl)silyl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol
• CAS No.: 204909-70-6
• Molecular Formula: C12H24O4Si
• Molecular Weight: 260.4
• European Community (EC) Number: 810-627-9
• Mol file: 204909-70-6.mol

Synonyms:204909-70-6;C12H24O4Si;(3R,3aR,6S,6aS)-6-[tert-butyl(dimethyl)silyl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol;(3R,3aR,6S,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-ol;MFCD20922751;SCHEMBL14967513;WS-00040;E71079;1,4:3,6-Dianhydro-2-O-[(1,1-dimethylethyl)dimethylsilyl]-D-glucitol;(3R,3AR,6S,6AS)-6-[(TERT-BUTYLDIMETHYLSILYL)OXY]-HEXAHYDROFURO[3,2-B]FURAN-3-OL

Chemical Property of (3R,3aR,6S,6aS)-6-[tert-butyl(dimethyl)silyl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol

Chemical Property:

• PSA: 47.92000
• LogP: 1.53530
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 260.14438578
• Heavy Atom Count: 17
• Complexity: 287

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1COC2C1OCC2O
• Isomeric SMILES: CC(C)(C)[Si](C)(C)O[C@H]1CO[C@H]2[C@@H]1OC[C@H]2O

Technology Process of (3R,3aR,6S,6aS)-6-[tert-butyl(dimethyl)silyl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol

There total 3 articles about (3R,3aR,6S,6aS)-6-[tert-butyl(dimethyl)silyl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol 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: 33.0%

tert-butyldimethylsilyl chloride (18162-48-6) + Isosorbide (652-67-5) → (3R,3aR,6S,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-ol (204909-70-6) + (3S,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-ol (479541-43-0) + 2,5-O,O'-bis(tert-butyldimethylsilyl)-1,4:3,6-dianhydro-D-sorbitole

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 40 ℃; for 3h;

DOI:10.1055/s-2003-41426

Reference yield: 28.0%

tert-butyldimethylsilyl chloride (18162-48-6) + Isosorbide (652-67-5) → (3R,3aR,6S,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-ol (204909-70-6) + (3S,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-ol (479541-43-0)

Guidance literature:

With 1H-imidazole; In water-d2; at 20 ℃;

Reference yield:

C12H23NO6Si → (3R,3aR,6S,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-ol (204909-70-6)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 24h;

DOI:10.1021/jm800564y

upstream raw materials:

tert-butyldimethylsilyl chloride

Isosorbide

Downstream raw materials:

C₁₄H₁₅NO₈

C₂₉H₄₀N₂O₉S

C₂₈H₃₉N₃O₈S

Benzoic acid (3S,3aR,5R,6R,6aS)-5-(6-chloro-purin-9-yl)-6-iodo-hexahydro-furo[3,2-b]furan-3-ylmethyl ester

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