6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose

Base Information

• Chemical Name: 6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose
• CAS No.: 848345-27-7
• Molecular Formula: C₂₅H₃₄O₆Si
• Molecular Weight: 458.627
• Mol file: 848345-27-7.mol

Synonyms:6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose

Chemical Property of 6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose

There total 1 articles about 6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose 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: 90.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 1,2-O-isopropylidene-β-L-idofuranose (29747-91-9) → 6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose (848345-27-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at -20 ℃; for 2h;

DOI:10.1016/j.tetasy.2004.11.034

Reference yield: 80.0%

6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose (848345-27-7) + benzyl bromide (100-39-0) → 3,5-di-O-benzyl-6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose (848345-28-8)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1016/j.tetasy.2004.11.034

Reference yield:

6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose (848345-27-7) → 3,5-di-O-benzyl-6-deoxy-6-nitro-β-L-idono-1,4-lactone (848345-33-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / sodium hydride; tetrabutylammonium iodide / dimethylformamide / 24 h / 20 °C

2: 94 percent / tetrabutylammonium fluoride / tetrahydrofuran / 38 h / 20 °C

3: 95 percent / pyridine / 10 h / 20 °C

4: 89 percent / sodium iodide / acetone / 15 h / Heating

5: 53 percent / sodium nitrite; 1,3,5-trihydroxybenzene / dimethylsulfoxide / 96 h / 20 °C

6: trifluoroacetic acid / H₂O / 16 h / 20 °C

7: 0.18 g / bromine; barium carbonate / dioxane; H₂O / 6 h

With pyridine; 3,5-dihydroxyphenol; tetrabutyl ammonium fluoride; bromine; tetra-(n-butyl)ammonium iodide; sodium hydride; barium carbonate; trifluoroacetic acid; sodium iodide; sodium nitrite; In tetrahydrofuran; 1,4-dioxane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tetasy.2004.11.034

upstream raw materials:

tert-butylchlorodiphenylsilane

1,2-O-isopropylidene-β-L-idofuranose

Downstream raw materials:

3,5-di-O-benzyl-6-O-t-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-idofuranose

(1S,4S,5R,6S,7R)-6,7-dibenzyloxy-5-nitro-2-oxabicyclo-[2.2.1]heptan-3-one

3,5-di-O-benzyl-6-deoxy-6-nitro-β-L-idono-1,4-lactone

methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-L-idofuranoside