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

Base Information

• Chemical Name: 3-O-benzyl-5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose
• CAS No.: 167500-61-0
• Molecular Formula: C₂₁H₃₄O₅Si
• Molecular Weight: 394.583
• Mol file: 167500-61-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about 3-O-benzyl-5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose 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%

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:

1,2-O-isopropylidene-α-D-xylose (20031-21-4) → 3-O-benzyl-5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose (167500-61-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / imidazole / dimethylformamide / 1 h / 0 °C

2: 98 percent / sodium hydride / dimethylformamide / 1 h / 0 °C

With 1H-imidazole; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.08.040

Reference yield:

D-xylose (58-86-6) → 3-O-benzyl-5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-xylofuranose (167500-61-0)

Guidance literature:

Multi-step reaction with 4 steps

1: CuSO₄; sulfuric acid / 12 h / 20 °C

2: 36.1 g / hydrochloric acid / H₂O / 1.5 h / 20 °C

3: 98 percent / imidazole / dimethylformamide / 1 h / 0 °C

4: 98 percent / sodium hydride / dimethylformamide / 1 h / 0 °C

With 1H-imidazole; hydrogenchloride; sulfuric acid; sodium hydride; copper(II) sulfate; In water; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.08.040

upstream raw materials:

benzyl bromide

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

D-xylose

1,2-O-isopropylidene-α-D-xylose

Downstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose

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

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

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