(3R,5R,7S,10R,11S,12R)-13-Benzyloxy-3,11-bis-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-tridec-1-ene-5,7-diol

Base Information

Chemical Name:(3R,5R,7S,10R,11S,12R)-13-Benzyloxy-3,11-bis-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-tridec-1-ene-5,7-diol
CAS No.:862096-26-2
Molecular Formula:C₃₄H₆₄O₅Si₂
Molecular Weight:609.05
Hs Code.:

Synonyms:(3R,5R,7S,10R,11S,12R)-13-Benzyloxy-3,11-bis-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-tridec-1-ene-5,7-diol

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Chemical Property of (3R,5R,7S,10R,11S,12R)-13-Benzyloxy-3,11-bis-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-tridec-1-ene-5,7-diol

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Technology Process of (3R,5R,7S,10R,11S,12R)-13-Benzyloxy-3,11-bis-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-tridec-1-ene-5,7-diol

There total 13 articles about (3R,5R,7S,10R,11S,12R)-13-Benzyloxy-3,11-bis-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-tridec-1-ene-5,7-diol 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:

: 69739-34-0
t-butyldimethylsiyl triflate

: 862096-26-2
(3R,5R,7S,10R,11S,12R)-13-Benzyloxy-3,11-bis-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-tridec-1-ene-5,7-diol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 83 percent / Et₃N / CH₂Cl₂ / 1 h / -30 - 0 °C

2.1: Rh(CO)2(acac); P(OPh)3; H₂

3.1: (R)-(+)-1,1'-bi-2-naphthol; titanium isopropoxide; 4 Angstroem MS / CH₂Cl₂ / 120 h / -20 °C

4.1: 91 percent / NaH; KI / tetrahydrofuran / 6 h / 0 °C

5.1: OsO₄; NMO; aq. t-BuOH / tetrahydrofuran / 1.5 h / 20 °C

5.2: 89 percent / NaIO₄ / tetrahydrofuran / 2 h / 20 °C

6.1: 83 percent / (C₆H₁₁)2BCl; Et₃N / diethyl ether / 22 h / -78 - -20 °C

7.1: 96 percent / 2,6-lutidine / tetrahydrofuran / 1 h / 0 °C

8.1: 89 percent / DDQ; buffer / CH₂Cl₂ / 0.67 h / 0 °C / pH 7

9.1: 85 percent / tetramethylammonium triacetoxyborohydride; AcOH / acetonitrile / 5 h / -15 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; triphenyl phosphite; acetylacetonatodicarbonylrhodium(l); osmium(VIII) oxide; N-methyl-2-indolinone; 4 Angstroem MS; dicyclohexylboron chloride; hydrogen; (R)-1,1'-Bi-2-naphthol; sodium hydride; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium iodide; tetramethylammonium triacetoxyborohydride; tert-butyl alcohol; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1016/j.tetlet.2005.04.146

Reference yield:

: 79026-61-2
(R)-3-benzyloxy-2-methylpropanal

: 862096-26-2
(3R,5R,7S,10R,11S,12R)-13-Benzyloxy-3,11-bis-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-tridec-1-ene-5,7-diol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 80 percent / TiCl₄ / 2.5 h / -90 °C

2.1: 83 percent / Et₃N / CH₂Cl₂ / 1 h / -30 - 0 °C

3.1: Rh(CO)2(acac); P(OPh)3; H₂

4.1: (R)-(+)-1,1'-bi-2-naphthol; titanium isopropoxide; 4 Angstroem MS / CH₂Cl₂ / 120 h / -20 °C

5.1: 91 percent / NaH; KI / tetrahydrofuran / 6 h / 0 °C

6.1: OsO₄; NMO; aq. t-BuOH / tetrahydrofuran / 1.5 h / 20 °C

6.2: 89 percent / NaIO₄ / tetrahydrofuran / 2 h / 20 °C

7.1: 83 percent / (C₆H₁₁)2BCl; Et₃N / diethyl ether / 22 h / -78 - -20 °C

8.1: 96 percent / 2,6-lutidine / tetrahydrofuran / 1 h / 0 °C

9.1: 89 percent / DDQ; buffer / CH₂Cl₂ / 0.67 h / 0 °C / pH 7

10.1: 85 percent / tetramethylammonium triacetoxyborohydride; AcOH / acetonitrile / 5 h / -15 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; triphenyl phosphite; acetylacetonatodicarbonylrhodium(l); osmium(VIII) oxide; N-methyl-2-indolinone; 4 Angstroem MS; dicyclohexylboron chloride; hydrogen; (R)-1,1'-Bi-2-naphthol; titanium tetrachloride; sodium hydride; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium iodide; tetramethylammonium triacetoxyborohydride; tert-butyl alcohol; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1016/j.tetlet.2005.04.146

Reference yield:

: 119065-12-2
(3R,4S,5R)-6-(benzyloxy)-3,5-dimethyl-1-hexen-4-ol

: 862096-26-2
(3R,5R,7S,10R,11S,12R)-13-Benzyloxy-3,11-bis-(tert-butyl-dimethyl-silanyloxy)-10,12-dimethyl-tridec-1-ene-5,7-diol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 83 percent / Et₃N / CH₂Cl₂ / 1 h / -30 - 0 °C

2.1: Rh(CO)2(acac); P(OPh)3; H₂

3.1: (R)-(+)-1,1'-bi-2-naphthol; titanium isopropoxide; 4 Angstroem MS / CH₂Cl₂ / 120 h / -20 °C

4.1: 91 percent / NaH; KI / tetrahydrofuran / 6 h / 0 °C

5.1: OsO₄; NMO; aq. t-BuOH / tetrahydrofuran / 1.5 h / 20 °C

5.2: 89 percent / NaIO₄ / tetrahydrofuran / 2 h / 20 °C

6.1: 83 percent / (C₆H₁₁)2BCl; Et₃N / diethyl ether / 22 h / -78 - -20 °C

7.1: 96 percent / 2,6-lutidine / tetrahydrofuran / 1 h / 0 °C

8.1: 89 percent / DDQ; buffer / CH₂Cl₂ / 0.67 h / 0 °C / pH 7

9.1: 85 percent / tetramethylammonium triacetoxyborohydride; AcOH / acetonitrile / 5 h / -15 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; triphenyl phosphite; acetylacetonatodicarbonylrhodium(l); osmium(VIII) oxide; N-methyl-2-indolinone; 4 Angstroem MS; dicyclohexylboron chloride; hydrogen; (R)-1,1'-Bi-2-naphthol; sodium hydride; acetic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium iodide; tetramethylammonium triacetoxyborohydride; tert-butyl alcohol; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1016/j.tetlet.2005.04.146