Toluene-4-sulfonic acid (1S,2R)-10-benzyloxy-1-{(S)-3-benzyloxy-3-[(2S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-((Z)-dec-3-enyl)-tetrahydro-pyran-2-yl]-propyl}-2-(tert-butyl-dimethyl-silanyloxy)-decyl ester

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Chemical Name:Toluene-4-sulfonic acid (1S,2R)-10-benzyloxy-1-{(S)-3-benzyloxy-3-[(2S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-((Z)-dec-3-enyl)-tetrahydro-pyran-2-yl]-propyl}-2-(tert-butyl-dimethyl-silanyloxy)-decyl ester
CAS No.:910058-05-8
Molecular Formula:C₆₁H₁₀₀O₈SSi₂
Molecular Weight:1049.7
Hs Code.:

Toluene-4-sulfonic acid (1S,2R)-10-benzyloxy-1-{(S)-3-benzyloxy-3-[(2S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-((Z)-dec-3-enyl)-tetrahydro-pyran-2-yl]-propyl}-2-(tert-butyl-dimethyl-silanyloxy)-decyl ester

Synonyms:Toluene-4-sulfonic acid (1S,2R)-10-benzyloxy-1-{(S)-3-benzyloxy-3-[(2S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-((Z)-dec-3-enyl)-tetrahydro-pyran-2-yl]-propyl}-2-(tert-butyl-dimethyl-silanyloxy)-decyl ester

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Chemical Property of Toluene-4-sulfonic acid (1S,2R)-10-benzyloxy-1-{(S)-3-benzyloxy-3-[(2S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-((Z)-dec-3-enyl)-tetrahydro-pyran-2-yl]-propyl}-2-(tert-butyl-dimethyl-silanyloxy)-decyl ester

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Technology Process of Toluene-4-sulfonic acid (1S,2R)-10-benzyloxy-1-{(S)-3-benzyloxy-3-[(2S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-((Z)-dec-3-enyl)-tetrahydro-pyran-2-yl]-propyl}-2-(tert-butyl-dimethyl-silanyloxy)-decyl ester

There total 21 articles about Toluene-4-sulfonic acid (1S,2R)-10-benzyloxy-1-{(S)-3-benzyloxy-3-[(2S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-((Z)-dec-3-enyl)-tetrahydro-pyran-2-yl]-propyl}-2-(tert-butyl-dimethyl-silanyloxy)-decyl ester 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%

: 910057-92-0
(2S,3R,6S)-6-[(1'S,4'S,5'R)-1',13'-dibenzyloxy-4'-hydroxy-5'-tert-butyldimethylsilyloxy-tridecanyl]-2-(Z)-dec-3''-enyl-3-tert-butyldimethylsilyloxy-tetrahydropyrane

: 98-59-9
p-toluenesulfonyl chloride

: 910058-05-8
Toluene-4-sulfonic acid (1S,2R)-10-benzyloxy-1-{(S)-3-benzyloxy-3-[(2S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-((Z)-dec-3-enyl)-tetrahydro-pyran-2-yl]-propyl}-2-(tert-butyl-dimethyl-silanyloxy)-decyl ester

Guidance literature:: With pyridine; dmap; at 0 - 20 ℃; for 21h;
DOI:10.1021/ol0614471

Reference yield:

: 910057-84-0
(S)-3-Benzyloxy-tetrahydro-furan-2-ol

: 910058-05-8
Toluene-4-sulfonic acid (1S,2R)-10-benzyloxy-1-{(S)-3-benzyloxy-3-[(2S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-((Z)-dec-3-enyl)-tetrahydro-pyran-2-yl]-propyl}-2-(tert-butyl-dimethyl-silanyloxy)-decyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 82 percent / MgBr₂*Et₂O; 1,2-dibromoethane / diethyl ether; CH₂Cl₂; tetrahydrofuran / 24 h / 20 °C

2.1: 93 percent / imidazole / CH₂Cl₂; toluene / 1 h / 20 °C

3.1: KH / tetrahydrofuran / -78 - 20 °C

3.2: 72 percent / MeLi / tetrahydrofuran; diethyl ether / 1.5 h / -78 - -40 °C

4.1: 70 percent / Cp₂ZrClH / CH₂Cl₂ / 24 h / 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 12 h / -100 - 20 °C

6.1: 79 percent / Yb(OTf)3; H₂O / acetonitrile / 20 °C

7.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 - -10 °C

8.1: H₂; Rh(CO)2(acac); BIPHEPHOS / tetrahydrofuran / 36 h / 50 °C / 6000.48 Torr

9.1: 125 mg / NaHMDS / tetrahydrofuran / 3.5 h / -78 - 20 °C

10.1: 86 percent / CSA / CH₂Cl₂; methanol / 1 h / 20 °C

11.1: 95 percent / pyridine; DMAP / CH₂Cl₂ / 3 h / 20 °C

12.1: 202 mg / NaI / acetone / 21 h / 20 - 50 °C

13.1: 53 percent / t-BuLi / diethyl ether; pentane / 3 h / -78 - -20 °C

14.1: 85 percent / pyridine; DMAP / 21 h / 0 - 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; acetylacetonatodicarbonylrhodium(l); Schwartz's reagent; n-butyllithium; camphor-10-sulfonic acid; water; hydrogen; tert.-butyl lithium; sodium hexamethyldisilazane; potassium hydride; 6,6′-[(3,3′-di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(di-benzo[d,f][1,3,2]dioxaphosphepin); ethylene dibromide; sodium iodide; magnesium bromide; ytterbium(III) triflate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetone; toluene; acetonitrile; pentane; 9.1: Wittig reaction;
DOI:10.1021/ol0614471

Reference yield:

: C₁₄H₂₁BrMgO

: 910058-05-8
Toluene-4-sulfonic acid (1S,2R)-10-benzyloxy-1-{(S)-3-benzyloxy-3-[(2S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-((Z)-dec-3-enyl)-tetrahydro-pyran-2-yl]-propyl}-2-(tert-butyl-dimethyl-silanyloxy)-decyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 77 percent / CuI / tetrahydrofuran / -30 - 0 °C

2: 84 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / -50 °C

3: 60 percent / CSA / CH₂Cl₂; methanol / 0.5 h / 20 °C

4: 85 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h / 20 °C

5: 53 percent / t-BuLi / diethyl ether; pentane / 3 h / -78 - -20 °C

6: 85 percent / pyridine; DMAP / 21 h / 0 - 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; copper(l) iodide; camphor-10-sulfonic acid; tert.-butyl lithium; Dess-Martin periodane; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; pentane; 4: Dess-Martin oxidation;
DOI:10.1021/ol0614471