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

Base Information

Chemical Name:5-O-(tert-butyldiphenylsilyl)-4-C-(2-ethoxycarbonyl-(E)-vinyl)-3-O-benzyl-1,2-O-isopropylidene-α-D-erythropentofuranose
CAS No.:634153-90-5
Molecular Formula:C₃₆H₄₄O₇Si
Molecular Weight:616.827
Hs Code.:

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

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

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

There total 1 articles about 5-O-(tert-butyldiphenylsilyl)-4-C-(2-ethoxycarbonyl-(E)-vinyl)-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:

: 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

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

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

Reference yield: 71.0%

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

: 3-[(3aR,5R,6S,6aR)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-propionic acid ethyl ester

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

Guidance literature:: With hydrogen; palladium on activated charcoal; In dichloromethane; for 10h; under 181.002 Torr;
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

: 5'-O-(4,4'-dimethoxytrityl)-2'-O,4'-C-propylene-5-methyluridine-3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite

Guidance literature:: Multi-step reaction with 9 steps

1.1: 71 percent / H₂ / palladium on carbon / CH₂Cl₂ / 10 h / 181 Torr

2.1: 85 percent / lithium tri-s-butylborohydride / tetrahydrofuran / 30 h / 20 °C

3.1: 77 percent / pyridine / CH₂Cl₂ / 20 °C

4.1: 79 percent / H₂SO₄; acetic acid / 0.5 h / 20 °C

5.1: 88 percent / trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 3 h / 50 °C

6.1: NaOH; pyridine / 0.33 h / 20 °C

6.2: 82 percent / tetrabutylammonium fluoride / tetrahydrofuran / 6 h / 20 °C

7.1: 59 percent / H₂ / palladium hydroxide on carbon / methanol

8.1: 100 percent / pyridine / 40 °C

9.1: 100 percent / N,N-diisopropylammonium tetrazolide / 20 °C

With pyridine; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; N,N-diisopropylamine tetrazolide; hydrogen; L-Selectride; acetic acid; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1016/S0968-0896(03)00115-9