Methyl-6-O-(tert.-butyldimethylsilyl)-2,3,4-tri-O-acetyl-α-D-glucopyranoside

Base Information

• Chemical Name: Methyl-6-O-(tert.-butyldimethylsilyl)-2,3,4-tri-O-acetyl-α-D-glucopyranoside
• CAS No.: 63734-11-2
• Molecular Formula: C19H34O9Si
• Molecular Weight: 434.555

Synonyms:Methyl-6-O-(tert.-butyldimethylsilyl)-2,3,4-tri-O-acetyl-α-D-glucopyranoside;Methyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-a-D-glucopyranoside

Chemical Property of Methyl-6-O-(tert.-butyldimethylsilyl)-2,3,4-tri-O-acetyl-α-D-glucopyranoside

Chemical Property:

• PSA: 106.59000
• LogP: 2.17460

Purity/Quality:

97% ^*data from raw suppliers

METHYL-2,3,4-TRI-O-ACETYL-6-O-TERT-BUTYLDIMETHYLSILYL-ALPHA-D-GLUCOPYRANOSIDE 95.00% ^*data from reagent suppliers

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Technology Process of Methyl-6-O-(tert.-butyldimethylsilyl)-2,3,4-tri-O-acetyl-α-D-glucopyranoside

There total 7 articles about Methyl-6-O-(tert.-butyldimethylsilyl)-2,3,4-tri-O-acetyl-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: 98.0%

acetic anhydride (108-24-7) + tert-butyldimethylsilyl chloride (18162-48-6) + methyl-alpha-D-glucopyranoside (97-30-3) → acetic acid 3,5-diacetoxy-2-(tert-butyldimethylsilanyloxymethyl)-6-methoxytetrahydropyran-4-yl ester (63734-11-2,594841-23-3)

Guidance literature:

tert-butyldimethylsilyl chloride; methyl-alpha-D-glucopyranoside; With dmap; In pyridine; at 20 ℃;

acetic anhydride; In pyridine; at 20 ℃;

DOI:10.1016/j.tet.2004.07.056

Reference yield: 92.0%

methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside (63734-12-3,74247-81-7,74247-82-8,74264-88-3) + acetic anhydride (108-24-7) → acetic acid 3,5-diacetoxy-2-(tert-butyldimethylsilanyloxymethyl)-6-methoxytetrahydropyran-4-yl ester (63734-11-2,594841-23-3)

Guidance literature:

With 1H-imidazole; In acetonitrile; at 20 ℃; for 3h;

DOI:10.1002/ejoc.200500555

Reference yield: 72.0%

methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside (63734-12-3,74247-81-7,74247-82-8,74264-88-3) + ethyl acetate (141-78-6) → acetic acid 3,5-diacetoxy-2-(tert-butyldimethylsilanyloxymethyl)-6-methoxytetrahydropyran-4-yl ester (63734-11-2,594841-23-3)

Guidance literature:

With C₁₆H₂₅N₃O₂S; for 36h; Molecular sieve; Reflux;

DOI:10.1021/acscatal.9b01959

upstream raw materials:

methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside

acetic anhydride

tert-butyldimethylsilyl chloride

methyl-alpha-D-glucopyranoside

Downstream raw materials:

methyl 1,2,4-tri-O-acetyl-6-O-benzyl-α-D-glucopyranoside

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