5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-ribofuranosyl trichloroacetamidate

Base Information

• Chemical Name: 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-ribofuranosyl trichloroacetamidate
• CAS No.: 478367-12-3
• Molecular Formula: C₂₆H₃₂Cl₃NO₅Si
• Molecular Weight: 572.988

Synonyms:5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-ribofuranosyl trichloroacetamidate

Chemical Property of 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-ribofuranosyl trichloroacetamidate

Chemical Property:

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Technology Process of 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-ribofuranosyl trichloroacetamidate

There total 2 articles about 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-ribofuranosyl trichloroacetamidate 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: 93.0%

trichloroacetonitrile (545-06-2) + 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose (96690-02-7) → 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-ribofuranosyl trichloroacetamidate (478367-12-3)

Guidance literature:

With caesium carbonate; In dichloromethane; at 18 ℃; for 5h;

DOI:10.1055/s-2003-41026

Reference yield: 43.0%

(3aR,6R,6aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol (138127-67-0) + trichloroacetonitrile (545-06-2) → 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-ribofuranosyl trichloroacetamidate (478367-12-3)

Guidance literature:

With caesium carbonate; In dichloromethane; at 18 ℃; for 5h;

Reference yield: 52.0%

pyrrole (109-97-7,30604-81-0) + 5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-ribofuranosyl trichloroacetamidate (478367-12-3) → 2-(5-O-tert-butyldiphenylsilyl-1-deoxy-2,3-O-isopropylidene-ribofuranosyl)pyrrole (629601-78-1)

Guidance literature:

boron trifluoride diethyl etherate; In diethyl ether; dichloromethane; at -78 - 18 ℃; for 2.33h;

upstream raw materials:

trichloroacetonitrile

5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribofuranose

(3aR,6R,6aR)-6-((tert-butyldiphenylsilyloxy)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol

Downstream raw materials:

3-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-1-triisopropylsilanyl-1H-pyrrole

3-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-1-triisopropylsilanyl-1H-pyrrole

showdomycin

3-[(3aS,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-pyrrole-2,5-dione

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