1-(4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-3,3-dimethyl-3-sila-1-butyne

Base Information

• Chemical Name: 1-(4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-3,3-dimethyl-3-sila-1-butyne
• CAS No.: 115029-78-2
• Molecular Formula: C₁₈H₂₂O₃Si
• Molecular Weight: 314.456
• Mol file: 115029-78-2.mol

Synonyms:1-(4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-3,3-dimethyl-3-sila-1-butyne

Chemical Property of 1-(4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-3,3-dimethyl-3-sila-1-butyne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-3,3-dimethyl-3-sila-1-butyne

There total 4 articles about 1-(4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-3,3-dimethyl-3-sila-1-butyne 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: 89.0%

benzaldehyde dimethyl acetal (1125-88-8) + 1-(2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-3,3-dimethyl-3-sila-1-butyne (115029-77-1) → 1-(4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-3,3-dimethyl-3-sila-1-butyne (115029-78-2)

Guidance literature:

With camphor-10-sulfonic acid; In N,N-dimethyl-formamide; at 100 ℃; for 6h;

DOI:10.1016/S0008-6215(00)90886-3

Reference yield:

((2R,3S,6S)-3-acetoxy-6-((trimethylsilyl)ethynyl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate (115029-76-0) → 1-(4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-3,3-dimethyl-3-sila-1-butyne (115029-78-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

2: 89 percent / camphorsulfonic acid / dimethylformamide / 6 h / 100 °C

With lithium aluminium tetrahydride; camphor-10-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)90886-3

Reference yield:

Bis(trimethylsilyl)ethyne (14630-40-1) → 1-(4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-3,3-dimethyl-3-sila-1-butyne (115029-78-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / TiCl₄ / CH₂Cl₂ / -20 °C

2: 94 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

3: 89 percent / camphorsulfonic acid / dimethylformamide / 6 h / 100 °C

With lithium aluminium tetrahydride; camphor-10-sulfonic acid; titanium tetrachloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)90886-3

upstream raw materials:

benzaldehyde dimethyl acetal

1-(2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-3,3-dimethyl-3-sila-1-butyne

((2R,3S,6S)-3-acetoxy-6-((trimethylsilyl)ethynyl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate

Bis(trimethylsilyl)ethyne

Downstream raw materials:

1-(4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hexopyranosyl)-3,3-dimethyl-3-sila-1-butene