tert-Butyl-((3aS,5R,6aS)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-diphenyl-silane

Base Information

• Chemical Name: tert-Butyl-((3aS,5R,6aS)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-diphenyl-silane
• CAS No.: 106799-16-0
• Molecular Formula: C₂₄H₃₂O₄Si
• Molecular Weight: 412.601
• Mol file: 106799-16-0.mol

Synonyms:tert-Butyl-((3aS,5R,6aS)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-diphenyl-silane

Chemical Property of tert-Butyl-((3aS,5R,6aS)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-((3aS,5R,6aS)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-diphenyl-silane

There total 5 articles about tert-Butyl-((3aS,5R,6aS)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-diphenyl-silane 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: 77.0%

Thiocarbonic acid O-[(3aS,5S,6R,6aS)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester O-phenyl ester (114861-15-3,150943-34-3) → tert-Butyl-((3aS,5R,6aS)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-diphenyl-silane (106799-16-0)

Guidance literature:

With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile); In toluene; at 80 ℃; for 1h;

DOI:10.1021/ja00241a062

Reference yield:

5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-L-xylofuranose (220827-73-6) → tert-Butyl-((3aS,5R,6aS)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-diphenyl-silane (106799-16-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / pyridine / DMAP / CH₂Cl₂ / 15 h / 0 - 25 °C

2: 77 percent / n-BuSnH / AIBN / toluene / 1 h / 80 °C

With pyridine; n-butyl tin hydride; dmap; 2,2'-azobis(isobutyronitrile); In dichloromethane; toluene;

DOI:10.1021/ja00222a028

Reference yield:

1,2-O-isopropylidene-α-L-xylofuranose (114861-22-2) → tert-Butyl-((3aS,5R,6aS)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethoxy)-diphenyl-silane (106799-16-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

2: 94 percent / pyridine / DMAP / CH₂Cl₂ / 15 h / 0 - 25 °C

3: 77 percent / n-BuSnH / AIBN / toluene / 1 h / 80 °C

With pyridine; 1H-imidazole; n-butyl tin hydride; dmap; 2,2'-azobis(isobutyronitrile); In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00222a028

upstream raw materials:

Thiocarbonic acid O-[(3aS,5S,6R,6aS)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester O-phenyl ester

5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-L-xylofuranose

tert-butylchlorodiphenylsilane

1,2-O-isopropylidene-α-L-xylofuranose

Downstream raw materials:

3-deoxy-1,2-O-(1-methylethylidene)-5-O-(phenylmethyl)-α-L-xylofuranose

3-deoxy-5-O-(phenylmethyl)-α-L-xylofuranose

<4R-(4α,5α)>-4-<(phenylmethoxy)methyl>-6-ethenyl-2,2-dimethyl-1,3-dioxane

(2R,4S)-1-<(phenylmethoxy)methyl>5-hexene-2,4-diol