3,6-O-bis(tert-butyldimethylsilanyl)-1-O-methyl-α-D-glucopyranoside

Base Information

• Chemical Name: 3,6-O-bis(tert-butyldimethylsilanyl)-1-O-methyl-α-D-glucopyranoside
• CAS No.: 68102-62-5
• Molecular Formula: C₁₉H₄₂O₆Si₂
• Molecular Weight: 422.71
• Mol file: 68102-62-5.mol

Synonyms:3,6-O-bis(tert-butyldimethylsilanyl)-1-O-methyl-α-D-glucopyranoside

Chemical Property of 3,6-O-bis(tert-butyldimethylsilanyl)-1-O-methyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,6-O-bis(tert-butyldimethylsilanyl)-1-O-methyl-α-D-glucopyranoside

There total 3 articles about 3,6-O-bis(tert-butyldimethylsilanyl)-1-O-methyl-α-D-glucopyranoside 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%

tert-butyldimethylsilane (29681-57-0) + methyl-alpha-D-glucopyranoside (97-30-3) → methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside (63734-12-3,74247-81-7,74247-82-8,74264-88-3) + 3,6-O-bis(tert-butyldimethylsilanyl)-1-O-methyl-α-D-glucopyranoside (68102-62-5) + 2,6-O-bis(tert-butyldimethylsilanyl)-1-O-methyl-α-D-glucopyranoside (68102-59-0) + 4,6-O-bis(tert-butyldimethylsilanyl)-1-O-methyl-α-D-glucopyranoside

Guidance literature:

With N,N-dimethyl acetamide; palladium dichloride; at 20 ℃; Further byproducts.;

DOI:10.1021/ja026723v

Reference yield: 62.0%

tert-butyldimethylsilane (29681-57-0) + (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol (617-04-9) → 2,6-O-bis(tert-butyldimethylsilanyl)-1-O-methyl-α-D-mannopyranoside (74247-79-3) + 3,6-O-bis(tert-butyldimethylsilanyl)-1-O-methyl-α-D-mannopyranoside (68102-62-5,68102-66-9,74247-72-6,116144-19-5,74247-74-8) + 6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-mannopyranoside (74247-81-7) + methyl 4,6-di-O-(tert-butyldimethylsilyl)-α-D-mannopyranoside (74247-89-5)

Guidance literature:

With N,N-dimethyl acetamide; palladium dichloride; at 20 ℃;

DOI:10.1021/ja026723v

Reference yield: 38.0%

tert-butyldimethylsilyl chloride (18162-48-6) + methyl-alpha-D-glucopyranoside (97-30-3) → methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside (63734-12-3,74247-81-7,74247-82-8,74264-88-3) + 3,6-O-bis(tert-butyldimethylsilanyl)-1-O-methyl-α-D-glucopyranoside (68102-62-5) + 2,6-O-bis(tert-butyldimethylsilanyl)-1-O-methyl-α-D-glucopyranoside (68102-59-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 24h; Product distribution; Ambient temperature; varying reagent mol ratio (2, 3, or 4 mol. equiv.); also other reagent (triethylamine and 4-dimethylaminopyridine); also from other methyl α- and β-D-aldohexapyranosides;

DOI:10.1016/0008-6215(87)85005-X

upstream raw materials:

tert-butyldimethylsilane

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

tert-butyldimethylsilyl chloride

methyl-alpha-D-glucopyranoside

Downstream raw materials:

methyl 2-O-(4-bromobenzoyl)-3,6-di-O-(tert-butyldimethylsilyl)-α-D-mannopyranoside

methyl 2,4-di-O-(4-bromobenzoyl)-3,6-di-O-(tert-butyldimethylsilyl)-α-D-mannopyranoside

methyl 2-O-(4-bromobenzoyl)-4-O-(4-methoxycinnamoyl)-α-D-mannopyranoside

(E)-3-(4-Methoxy-phenyl)-acrylic acid (2S,3S,4S,5S,6R)-4-hydroxy-6-hydroxymethyl-2-methoxy-5-[(E)-3-(4-methoxy-phenyl)-acryloyloxy]-tetrahydro-pyran-3-yl ester