5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-{[(4-methylphenyl)sulfonyl]oxy}propyl-3-O-benzyl-1,2-O-(1-methylethylidene)-α-D-ribofuranose

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Chemical Name:5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-{[(4-methylphenyl)sulfonyl]oxy}propyl-3-O-benzyl-1,2-O-(1-methylethylidene)-α-D-ribofuranose
CAS No.:634153-93-8
Molecular Formula:C₄₁H₅₀O₈SSi
Molecular Weight:730.995
Hs Code.:

Synonyms:5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-{[(4-methylphenyl)sulfonyl]oxy}propyl-3-O-benzyl-1,2-O-(1-methylethylidene)-α-D-ribofuranose

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Chemical Property of 5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-{[(4-methylphenyl)sulfonyl]oxy}propyl-3-O-benzyl-1,2-O-(1-methylethylidene)-α-D-ribofuranose

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Technology Process of 5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-{[(4-methylphenyl)sulfonyl]oxy}propyl-3-O-benzyl-1,2-O-(1-methylethylidene)-α-D-ribofuranose

There total 4 articles about 5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-{[(4-methylphenyl)sulfonyl]oxy}propyl-3-O-benzyl-1,2-O-(1-methylethylidene)-α-D-ribofuranose 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:

: 212970-72-4
{3-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-(1S,3R,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)bicyclo[3.3.0]oct-3-yl}methan-1-ol

: 634153-93-8
5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-{[(4-methylphenyl)sulfonyl]oxy}propyl-3-O-benzyl-1,2-O-(1-methylethylidene)-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

2: 86 percent / sodium hydride / tetrahydrofuran / 0.5 h / 20 °C

3: 71 percent / H₂ / palladium on carbon / CH₂Cl₂ / 10 h / 181 Torr

4: 85 percent / lithium tri-s-butylborohydride / tetrahydrofuran / 30 h / 20 °C

5: 77 percent / pyridine / CH₂Cl₂ / 20 °C

With pyridine; oxalyl dichloride; hydrogen; L-Selectride; sodium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; 1: Swern oxidation / 2: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/S0968-0896(03)00115-9

Reference yield:

: 454715-80-1
5-O-(tert-butyldiphenylsilyl)-3-O-benzyl-4-C-formyl-1,2-O-isopropylidene-α-D-erythropentofuranose

: 634153-93-8
5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-{[(4-methylphenyl)sulfonyl]oxy}propyl-3-O-benzyl-1,2-O-(1-methylethylidene)-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / sodium hydride / tetrahydrofuran / 0.5 h / 20 °C

2: 71 percent / H₂ / palladium on carbon / CH₂Cl₂ / 10 h / 181 Torr

3: 85 percent / lithium tri-s-butylborohydride / tetrahydrofuran / 30 h / 20 °C

4: 77 percent / pyridine / CH₂Cl₂ / 20 °C

With pyridine; hydrogen; L-Selectride; sodium hydride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; 1: Horner-Wadsworth-Emmons olefination;
DOI:10.1016/S0968-0896(03)00115-9

Reference yield:

: 634153-90-5
5-O-(tert-butyldiphenylsilyl)-4-C-(2-ethoxycarbonyl-(E)-vinyl)-3-O-benzyl-1,2-O-isopropylidene-α-D-erythropentofuranose

: 634153-93-8
5-O-[(1,1-dimethylethyl)diphenylsilyl]-4-C-{[(4-methylphenyl)sulfonyl]oxy}propyl-3-O-benzyl-1,2-O-(1-methylethylidene)-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 3 steps

1: 71 percent / H₂ / palladium on carbon / CH₂Cl₂ / 10 h / 181 Torr

2: 85 percent / lithium tri-s-butylborohydride / tetrahydrofuran / 30 h / 20 °C

3: 77 percent / pyridine / CH₂Cl₂ / 20 °C

With pyridine; hydrogen; L-Selectride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0968-0896(03)00115-9