5-O-(tert-butyldiphenylsilyl)-4-C-hydroxypropyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythropentofuranose

Base Information

Chemical Name:5-O-(tert-butyldiphenylsilyl)-4-C-hydroxypropyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythropentofuranose
CAS No.:634153-92-7
Molecular Formula:C₃₄H₄₄O₆Si
Molecular Weight:576.805
Hs Code.:

Synonyms:5-O-(tert-butyldiphenylsilyl)-4-C-hydroxypropyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythropentofuranose

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Chemical Property of 5-O-(tert-butyldiphenylsilyl)-4-C-hydroxypropyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythropentofuranose

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Technology Process of 5-O-(tert-butyldiphenylsilyl)-4-C-hydroxypropyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythropentofuranose

There total 4 articles about 5-O-(tert-butyldiphenylsilyl)-4-C-hydroxypropyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythropentofuranose 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: 85.0%

: 634153-91-6
5-O-(tert-butyldiphenylsilyl)-4-C-(2-ethoxycarbonylethyl)-3-O-benzyl-1,2-O-isopropylidene-α-D-erythropentofuranose

: 634153-92-7
5-O-(tert-butyldiphenylsilyl)-4-C-hydroxypropyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythropentofuranose

Guidance literature:: With L-Selectride; In tetrahydrofuran; at 20 ℃; for 30h;
DOI:10.1016/S0968-0896(03)00115-9

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

: 634153-92-7
5-O-(tert-butyldiphenylsilyl)-4-C-hydroxypropyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythropentofuranose

Guidance literature:: Multi-step reaction with 4 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

With 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

: 634153-92-7
5-O-(tert-butyldiphenylsilyl)-4-C-hydroxypropyl-3-O-benzyl-1,2-O-isopropylidene-α-D-erythropentofuranose

Guidance literature:: Multi-step reaction with 3 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

With 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