S-ethyl (4E,7R)-7-C-allyl-6,7-O-(4-{[tert-butyl(dimethyl)silyl]oxy}benzylidene)-2,4,5-trideoxy-2-ethyl-1-thio-3-O-(triethylsilyl)-6-C-[2-(trityloxy)ethyl]-L-arabino-4-enoate

Base Information

Chemical Name:S-ethyl (4E,7R)-7-C-allyl-6,7-O-(4-{[tert-butyl(dimethyl)silyl]oxy}benzylidene)-2,4,5-trideoxy-2-ethyl-1-thio-3-O-(triethylsilyl)-6-C-[2-(trityloxy)ethyl]-L-arabino-4-enoate
CAS No.:521274-41-9
Molecular Formula:C₅₄H₇₄O₆SSi₂
Molecular Weight:907.415
Hs Code.:

S-ethyl (4E,7R)-7-C-allyl-6,7-O-(4-{[tert-butyl(dimethyl)silyl]oxy}benzylidene)-2,4,5-trideoxy-2-ethyl-1-thio-3-O-(triethylsilyl)-6-C-[2-(trityloxy)ethyl]-L-arabino-4-enoate

Synonyms:S-ethyl (4E,7R)-7-C-allyl-6,7-O-(4-{[tert-butyl(dimethyl)silyl]oxy}benzylidene)-2,4,5-trideoxy-2-ethyl-1-thio-3-O-(triethylsilyl)-6-C-[2-(trityloxy)ethyl]-L-arabino-4-enoate

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Chemical Property of S-ethyl (4E,7R)-7-C-allyl-6,7-O-(4-{[tert-butyl(dimethyl)silyl]oxy}benzylidene)-2,4,5-trideoxy-2-ethyl-1-thio-3-O-(triethylsilyl)-6-C-[2-(trityloxy)ethyl]-L-arabino-4-enoate

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Technology Process of S-ethyl (4E,7R)-7-C-allyl-6,7-O-(4-{[tert-butyl(dimethyl)silyl]oxy}benzylidene)-2,4,5-trideoxy-2-ethyl-1-thio-3-O-(triethylsilyl)-6-C-[2-(trityloxy)ethyl]-L-arabino-4-enoate

There total 19 articles about S-ethyl (4E,7R)-7-C-allyl-6,7-O-(4-{[tert-butyl(dimethyl)silyl]oxy}benzylidene)-2,4,5-trideoxy-2-ethyl-1-thio-3-O-(triethylsilyl)-6-C-[2-(trityloxy)ethyl]-L-arabino-4-enoate 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:

: 120743-99-9
p-[(tert-butyldimethylsilyl)oxy]benzaldehyde

: 521274-41-9
S-ethyl (4E,7R)-7-C-allyl-6,7-O-(4-{[tert-butyl(dimethyl)silyl]oxy}benzylidene)-2,4,5-trideoxy-2-ethyl-1-thio-3-O-(triethylsilyl)-6-C-[2-(trityloxy)ethyl]-L-arabino-4-enoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 6.82 g / CSA / methanol / 20 h / 23 °C

2.1: CSA / dimethylformamide / 0.67 h / 50 °C

3.1: 4.67 g / TBAF / tetrahydrofuran / 1.5 h / 20 °C

4.1: MnO₂ / CH₂Cl₂ / 3 h / 20 °C

5.1: 2.51 g / imidazole / CH₂Cl₂ / 1 h / 20 °C

6.1: n-Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 0.67 h / 0 °C

6.2: CH₂Cl₂ / 5 h / -78 - 20 °C

7.1: imidazole / dimethylformamide / 0.08 h / 20 °C

8.1: 1.02 g / tetrahydrofuran; hexane / 1.5 h / 0 °C

With 1H-imidazole; manganese(IV) oxide; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja0340679

Reference yield:

: 118736-04-2
(4-(dimethoxymethyl)phenoxy)(tert-butyl)dimethylsilane

: 521274-41-9
S-ethyl (4E,7R)-7-C-allyl-6,7-O-(4-{[tert-butyl(dimethyl)silyl]oxy}benzylidene)-2,4,5-trideoxy-2-ethyl-1-thio-3-O-(triethylsilyl)-6-C-[2-(trityloxy)ethyl]-L-arabino-4-enoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: CSA / dimethylformamide / 0.67 h / 50 °C

2.1: 4.67 g / TBAF / tetrahydrofuran / 1.5 h / 20 °C

3.1: MnO₂ / CH₂Cl₂ / 3 h / 20 °C

4.1: 2.51 g / imidazole / CH₂Cl₂ / 1 h / 20 °C

5.1: n-Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 0.67 h / 0 °C

5.2: CH₂Cl₂ / 5 h / -78 - 20 °C

6.1: imidazole / dimethylformamide / 0.08 h / 20 °C

7.1: 1.02 g / tetrahydrofuran; hexane / 1.5 h / 0 °C

With 1H-imidazole; manganese(IV) oxide; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja0340679

Reference yield:

: 521274-19-1
(4-hydroxymethyl-2,2-dimethyl-[1,3]-dioxan-4-yl)-methanol

: 521274-41-9
S-ethyl (4E,7R)-7-C-allyl-6,7-O-(4-{[tert-butyl(dimethyl)silyl]oxy}benzylidene)-2,4,5-trideoxy-2-ethyl-1-thio-3-O-(triethylsilyl)-6-C-[2-(trityloxy)ethyl]-L-arabino-4-enoate

Guidance literature:: Multi-step reaction with 18 steps

1.1: lipase AK / hexane; H₂O / 17 h / 20 °C

1.2: imidazole / dimethylformamide / 1.5 h / 20 °C

2.1: K₂CO₃; MeOH / 2.5 h / 20 °C

3.1: TPAP; NMO; 4 A molecular sieves / CH₂Cl₂ / 1.17 h / 20 °C

4.1: toluene / 11 h / 100 °C

5.1: DIBAL / CH₂Cl₂; toluene / 0.17 h / -78 °C

6.1: TBAF / tetrahydrofuran / 20 °C

7.1: imidazole / CH₂Cl₂ / 2 h / 0 °C

8.1: TPAP; NMO; 4 A molecular sieves / CH₂Cl₂ / 3 h / 20 °C

9.1: 8.12 g / diethyl ether / -78 °C

10.1: PPTS / methanol / 0.67 h / 20 °C

11.1: pyridine; DMAP / 6 h / 50 °C

12.1: CSA / dimethylformamide / 0.67 h / 50 °C

13.1: 4.67 g / TBAF / tetrahydrofuran / 1.5 h / 20 °C

14.1: MnO₂ / CH₂Cl₂ / 3 h / 20 °C

15.1: 2.51 g / imidazole / CH₂Cl₂ / 1 h / 20 °C

16.1: n-Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 0.67 h / 0 °C

16.2: CH₂Cl₂ / 5 h / -78 - 20 °C

17.1: imidazole / dimethylformamide / 0.08 h / 20 °C

18.1: 1.02 g / tetrahydrofuran; hexane / 1.5 h / 0 °C

With pyridine; 1H-imidazole; methanol; dmap; manganese(IV) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; lipase AK; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 4.1: Wittig reaction;
DOI:10.1021/ja0340679