tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane

Base Information

• Chemical Name: tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane
• CAS No.: 378238-89-2
• Molecular Formula: C₂₈H₃₈O₆Si
• Molecular Weight: 498.692
• Mol file: 378238-89-2.mol

Synonyms:tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane

Chemical Property of tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane

There total 1 articles about tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-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: 99.0%

tert-butylchlorodiphenylsilane (58479-61-1) + Diacetone D-glucose (2595-05-3) → tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane (378238-89-2)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 18h;

DOI:10.1021/ol0167210

Reference yield: 96.0%

tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane (378238-89-2) → 3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose (378238-76-7)

Guidance literature:

tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane; With acetic acid; In water; at 20 ℃; for 48h;

With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 5h; Further stages.;

DOI:10.1021/ol0167210

Reference yield:

tert-Butyl-[(3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy]-diphenyl-silane (378238-89-2) → tert-Butyl-{(3aR,6S,6aR)-5-[1-iodo-meth-(E)-ylidene]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy}-diphenyl-silane (378238-77-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: AcOH / H₂O / 48 h / 20 °C

1.2: 96 percent / NaIO₄ / H₂O; tetrahydrofuran / 5 h / 20 °C

2.1: 100 percent / hydrazine hydrate / ethanol / 0.5 h / 100 °C

3.1: I₂; 1,1,3,3-tetramethylguanidine / diethyl ether / 1 h

3.2: DBU / toluene / 20 h / 60 °C

With iodine; hydrazine hydrate; acetic acid; N,N,N',N'-tetramethylguanidine; In diethyl ether; ethanol; water;

DOI:10.1021/ol0167210

upstream raw materials:

tert-butylchlorodiphenylsilane

Diacetone D-glucose

Downstream raw materials:

3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

tert-Butyl-{(3aR,6S,6aR)-5-[1-iodo-meth-(E)-ylidene]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy}-diphenyl-silane

[1-[(3aR,5R,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-meth-(E)-ylidene]-hydrazine

(3aR,3bS,5S,6S,6aR,7aR)-5-Ethoxycarbonylmethyl-2,2-dimethyl-6-phenylsulfanyl-hexahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxole-5-carboxylic acid ethyl ester