(5S,6S)-6-(4-methoxybenzyloxy)-13,13,14,14-tetramethyl-5-(prop-1-ynyl)-6-(trityloxymethyl)-2,4,12-trioxa-13-silapentadec-9-yne

Base Information

Chemical Name:(5S,6S)-6-(4-methoxybenzyloxy)-13,13,14,14-tetramethyl-5-(prop-1-ynyl)-6-(trityloxymethyl)-2,4,12-trioxa-13-silapentadec-9-yne
CAS No.:1403953-45-6
Molecular Formula:C₄₆H₅₆O₆Si
Molecular Weight:733.033
Hs Code.:

Synonyms:(5S,6S)-6-(4-methoxybenzyloxy)-13,13,14,14-tetramethyl-5-(prop-1-ynyl)-6-(trityloxymethyl)-2,4,12-trioxa-13-silapentadec-9-yne

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Chemical Property of (5S,6S)-6-(4-methoxybenzyloxy)-13,13,14,14-tetramethyl-5-(prop-1-ynyl)-6-(trityloxymethyl)-2,4,12-trioxa-13-silapentadec-9-yne

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Technology Process of (5S,6S)-6-(4-methoxybenzyloxy)-13,13,14,14-tetramethyl-5-(prop-1-ynyl)-6-(trityloxymethyl)-2,4,12-trioxa-13-silapentadec-9-yne

There total 11 articles about (5S,6S)-6-(4-methoxybenzyloxy)-13,13,14,14-tetramethyl-5-(prop-1-ynyl)-6-(trityloxymethyl)-2,4,12-trioxa-13-silapentadec-9-yne 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: 80.0%

: 1403953-34-3
(4S,5S)-10-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-5-(trityloxymethyl)deca-2,8-diyn-4-ol

: 107-30-2
chloromethyl methyl ether

: 1403953-45-6
(5S,6S)-6-(4-methoxybenzyloxy)-13,13,14,14-tetramethyl-5-(prop-1-ynyl)-6-(trityloxymethyl)-2,4,12-trioxa-13-silapentadec-9-yne

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 4h;
DOI:10.1039/c2ob26194d

Reference yield:

: 742104-83-2
(R)-{2-[(triphenylmethoxy)methyl]oxiran-2-yl}methanol

: 1403953-45-6
(5S,6S)-6-(4-methoxybenzyloxy)-13,13,14,14-tetramethyl-5-(prop-1-ynyl)-6-(trityloxymethyl)-2,4,12-trioxa-13-silapentadec-9-yne

Guidance literature:: Multi-step reaction with 10 steps

1.1: magnesium; mercury dichloride; iodine / diethyl ether; toluene / 3 h / 0 - 20 °C

1.2: 4 h / -78 - 20 °C

2.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h / 20 °C

2.2: 0.5 h

2.3: 0.5 h / 0 °C

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 0.67 h / -78 - 20 °C

4.1: 1H-imidazole / dichloromethane / 1 h / 20 °C

5.1: diisobutylaluminium hydride / cyclohexane / 1 h / -78 °C

6.1: Dess-Martin periodane / dichloromethane / 0.75 h / 20 °C

7.1: tetrahydrofuran / 2 h / -78 - 20 °C

8.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

9.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene; tetrahydrofuran / 1 h / -30 °C

10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C

With 1H-imidazole; n-butyllithium; dimethylsulfide borane complex; iodine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; magnesium; N-ethyl-N,N-diisopropylamine; mercury dichloride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; toluene;
DOI:10.1039/c2ob26194d

Reference yield:

: 510730-17-3
2-[(triphenylmethoxy)methyl]prop-2-en-1-ol

: 1403953-45-6
(5S,6S)-6-(4-methoxybenzyloxy)-13,13,14,14-tetramethyl-5-(prop-1-ynyl)-6-(trityloxymethyl)-2,4,12-trioxa-13-silapentadec-9-yne

Guidance literature:: Multi-step reaction with 11 steps

1.1: tert.-butylhydroperoxide; titanium(IV) isopropylate; diethyl (2R,3R)-tartrate / dichloromethane / -20 °C / Molecular sieve

2.1: magnesium; mercury dichloride; iodine / diethyl ether; toluene / 3 h / 0 - 20 °C

2.2: 4 h / -78 - 20 °C

3.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h / 20 °C

3.2: 0.5 h

3.3: 0.5 h / 0 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

4.2: 0.67 h / -78 - 20 °C

5.1: 1H-imidazole / dichloromethane / 1 h / 20 °C

6.1: diisobutylaluminium hydride / cyclohexane / 1 h / -78 °C

7.1: Dess-Martin periodane / dichloromethane / 0.75 h / 20 °C

8.1: tetrahydrofuran / 2 h / -78 - 20 °C

9.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C

10.1: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / toluene; tetrahydrofuran / 1 h / -30 °C

11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 4 h / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; diethyl (2R,3R)-tartrate; dimethylsulfide borane complex; iodine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; magnesium; N-ethyl-N,N-diisopropylamine; mercury dichloride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; toluene; 1.1: |Sharpless Asymmetric Epoxidation;
DOI:10.1039/c2ob26194d