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

Base Information

Chemical Name:(4S,5S)-10-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-5-(trityloxymethyl)deca-2,8-diyn-4-ol
CAS No.:1403953-34-3
Molecular Formula:C₄₄H₅₂O₅Si
Molecular Weight:688.979
Hs Code.:

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

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Chemical Property of (4S,5S)-10-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-5-(trityloxymethyl)deca-2,8-diyn-4-ol

Chemical Property:

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Technology Process of (4S,5S)-10-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-5-(trityloxymethyl)deca-2,8-diyn-4-ol

There total 9 articles about (4S,5S)-10-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-5-(trityloxymethyl)deca-2,8-diyn-4-ol 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:

: 1403953-44-5
(5S)-10-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-5-(trityloxymethyl)deca-2,8-diyn-4-one

: 1403953-43-4
(4R,5S)-10-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-5-(trityloxymethyl)deca-2,8-diyn-4-ol

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

Guidance literature:: With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at -30 ℃; for 1h; Overall yield = 78 %; Overall yield = 250 mg;
DOI:10.1039/c2ob26194d

Reference yield:

: 1403953-32-1
(2R)-7-(tert-butyldimethylsilyloxy)-2-(4-methoxybenzyloxy)-2-(trityloxymethyl)hept-5-yn-1-ol

: 1403953-43-4
(4R,5S)-10-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-5-(trityloxymethyl)deca-2,8-diyn-4-ol

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

Guidance literature:: Multi-step reaction with 4 steps

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

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

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

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

With dimethylsulfide borane complex; Dess-Martin periodane; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1039/c2ob26194d

Reference yield:

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

: 1403953-43-4
(4R,5S)-10-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-5-(trityloxymethyl)deca-2,8-diyn-4-ol

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

Guidance literature:: Multi-step reaction with 9 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

With 1H-imidazole; n-butyllithium; dimethylsulfide borane complex; iodine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; magnesium; 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