1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside

Base Information

• Chemical Name: 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside
• CAS No.: 85951-12-8
• Molecular Formula: C₁₄H₂₈O₅Si
• Molecular Weight: 304.459
• Mol file: 85951-12-8.mol

Synonyms:1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside

Chemical Property of 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside

There total 1 articles about 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside 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: 50.0%

tert-Butyl-[(3aR,5R,6S,6aR)-6-(3,4-dimethoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy]-dimethyl-silane (126308-94-9) → 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside (85951-12-8) + 3,4-Dimethoxy-benzoic acid (3aR,5R,6S,6aR)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (126308-95-0)

Guidance literature:

With magnesium(II) perchlorate; 9,10-Dicyanoanthracene; 9,10-phenanthrenequinone; In acetonitrile; for 2h; Irradiation;

Reference yield: 98.0%

benzyl bromide (100-39-0) + 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside (85951-12-8) → 3-O-benzyl-5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose (167500-61-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1016/j.bmc.2005.08.040

Reference yield: 29.0%

ethyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl disulfide (870472-11-0) + N-iodo-succinimide (516-12-1) + 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside (85951-12-8) → 1,2-O-isopropylidene-5-O-tert-butyldimethylsilyl-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-xylofuranose + 1,2-O-isopropylidene-5-O-tert-butyldimethylsilyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-xylofuranose + N-succinimidyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

Guidance literature:

With 2,4,5-tri-tert-butylpyrimidine; 4 A molecular sieve; triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at 20 ℃; for 22h;

DOI:10.1021/jo051374j

upstream raw materials:

tert-Butyl-[(3aR,5R,6S,6aR)-6-(3,4-dimethoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy]-dimethyl-silane

Downstream raw materials:

3-O-benzyl-5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose

methyl 3-O-benzyl-α-D-xylo-pentofuranoside

methyl 2,5-anhydro-3-O-benzyl-2,5-dideoxy-2-thio-β-D-arabino-pentofuranoside

methyl 2,5-anhydro-3-O-benzyl-2,5-dideoxy-2-thio-α-D-arabino-pentofuranoside