3-(2-{(S)-2-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-1-{2-[2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-[1,3]dithian-2-yl}-propan-1-one

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Chemical Name:3-(2-{(S)-2-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-1-{2-[2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-[1,3]dithian-2-yl}-propan-1-one
CAS No.:392663-32-0
Molecular Formula:C₄₇H₇₄O₈S₂Si₂
Molecular Weight:887.403
Hs Code.:

3-(2-{(S)-2-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-1-{2-[2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-[1,3]dithian-2-yl}-propan-1-one

Synonyms:3-(2-{(S)-2-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-1-{2-[2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-[1,3]dithian-2-yl}-propan-1-one

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Chemical Property of 3-(2-{(S)-2-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-1-{2-[2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-[1,3]dithian-2-yl}-propan-1-one

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Technology Process of 3-(2-{(S)-2-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-1-{2-[2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-[1,3]dithian-2-yl}-propan-1-one

There total 20 articles about 3-(2-{(S)-2-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-1-{2-[2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-[1,3]dithian-2-yl}-propan-1-one 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: 88.0%

: 392663-30-8
3-(2-{(S)-2-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-1-{2-[2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-[1,3]dithian-2-yl}-propan-1-ol

: 392663-32-0
3-(2-{(S)-2-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-1-{2-[2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-[1,3]dithian-2-yl}-propan-1-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 25 ℃; for 1h;
DOI:10.1002/1521-3773(20011105)40

Reference yield:

: 157240-43-2
(4R)-4,5-isopropylidenedioxy-1-(dimethoxyphosphoryl)-2-pentanone

: 392663-32-0
3-(2-{(S)-2-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-1-{2-[2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-[1,3]dithian-2-yl}-propan-1-one

Guidance literature:: Multi-step reaction with 15 steps

1.1: LiCl; N,N-diisopropylethylamine / acetonitrile / 2 h / 25 °C

1.2: 86 percent / acetonitrile / 15 h / 25 °C

2.1: 98 percent / LiI; LiAlH₄ / diethyl ether / -100 - 0 °C

3.1: 97 percent / AcOH / H₂O / 5 h / 40 °C

4.1: 70 percent / NaHCO₃; N-iodosuccinimide / tetrahydrofuran / 36 h / 0 °C

5.1: 99 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 10 h / 25 °C

6.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 99 percent / H₂; Raney-Ni catalyst / ethanol / 1 h / 25 °C

8.1: 88 percent / H₂ / Pd(OH)2/C / ethanol / 3 h / 25 °C

9.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 25 °C

10.1: Mg / tetrahydrofuran / 2 h / 25 °C

10.2: tetrahydrofuran / 2 h / -78 - 0 °C

11.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 - 25 °C

12.1: 98 percent / triethyl orthoformate; p-TsOH / 2.5 h / 55 °C

13.1: N-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 14 h / 25 °C

13.2: 100 percent / NaIO₄; aq. saline solution buffer / tetrahydrofuran; 2-methyl-propan-2-ol / 5 h / 25 °C

14.1: n-BuLi / tetrahydrofuran; toluene / 3 h / -30 °C

14.2: tetrahydrofuran / 1 h / -30 °C

15.1: 13.2 g / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; N-iodo-succinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; Raney-Ni catalyst; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; magnesium; acetic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; orthoformic acid triethyl ester; lithium chloride; lithium iodide; palladium dihydroxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1021/ja0547477

Reference yield:

: 392663-03-5
(E)-(2R,4S,7S)-8-Benzyloxy-7-methyl-oct-5-ene-1,2,4-triol

: 392663-32-0
3-(2-{(S)-2-[(2S,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1-methyl-ethyl}-[1,3]dioxolan-2-yl)-1-{2-[2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-[1,3]dithian-2-yl}-propan-1-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: 70 percent / NaHCO₃; N-iodosuccinimide / tetrahydrofuran / 36 h / 0 °C

2.1: 99 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 10 h / 25 °C

3.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 99 percent / H₂; Raney-Ni catalyst / ethanol / 1 h / 25 °C

5.1: 88 percent / H₂ / Pd(OH)2/C / ethanol / 3 h / 25 °C

6.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 25 °C

7.1: Mg / tetrahydrofuran / 2 h / 25 °C

7.2: tetrahydrofuran / 2 h / -78 - 0 °C

8.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 - 25 °C

9.1: 98 percent / triethyl orthoformate; p-TsOH / 2.5 h / 55 °C

10.1: N-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 14 h / 25 °C

10.2: 100 percent / NaIO₄; aq. saline solution buffer / tetrahydrofuran; 2-methyl-propan-2-ol / 5 h / 25 °C

11.1: n-BuLi / tetrahydrofuran; toluene / 3 h / -30 °C

11.2: tetrahydrofuran / 1 h / -30 °C

12.1: 13.2 g / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; N-iodo-succinimide; osmium(VIII) oxide; n-butyllithium; Raney-Ni catalyst; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; magnesium; 4-methylmorpholine N-oxide; triethylamine; orthoformic acid triethyl ester; palladium dihydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; tert-butyl alcohol;
DOI:10.1021/ja0547477