(2R,3S,5Z,8R,9S)-3-benzyloxy-2-benzyloxymethyl-8-(tret-butyldimethylsilyloxy)-9-(but-2'-ynyl)-2,3,4,7,8,9-hexahydrooxonin

Base Information

Chemical Name:(2R,3S,5Z,8R,9S)-3-benzyloxy-2-benzyloxymethyl-8-(tret-butyldimethylsilyloxy)-9-(but-2'-ynyl)-2,3,4,7,8,9-hexahydrooxonin
CAS No.:876288-82-3
Molecular Formula:C₃₃H₄₆O₄Si
Molecular Weight:534.811
Hs Code.:

Synonyms:(2R,3S,5Z,8R,9S)-3-benzyloxy-2-benzyloxymethyl-8-(tret-butyldimethylsilyloxy)-9-(but-2'-ynyl)-2,3,4,7,8,9-hexahydrooxonin

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Chemical Property of (2R,3S,5Z,8R,9S)-3-benzyloxy-2-benzyloxymethyl-8-(tret-butyldimethylsilyloxy)-9-(but-2'-ynyl)-2,3,4,7,8,9-hexahydrooxonin

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Technology Process of (2R,3S,5Z,8R,9S)-3-benzyloxy-2-benzyloxymethyl-8-(tret-butyldimethylsilyloxy)-9-(but-2'-ynyl)-2,3,4,7,8,9-hexahydrooxonin

There total 10 articles about (2R,3S,5Z,8R,9S)-3-benzyloxy-2-benzyloxymethyl-8-(tret-butyldimethylsilyloxy)-9-(but-2'-ynyl)-2,3,4,7,8,9-hexahydrooxonin 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: 99.0%

: 876288-81-2
(2R,3S,5Z,8R,9S)-[8-benzyloxy-9-benzyloxymethyl-3-(tret-butyldimethylsilyloxy)-2,3,4,7,8,9-hexahydrooxonin-2-yl]methyl trifluoromethanesulfonate

: 74-99-7
prop-1-yne

: 876288-82-3
(2R,3S,5Z,8R,9S)-3-benzyloxy-2-benzyloxymethyl-8-(tret-butyldimethylsilyloxy)-9-(but-2'-ynyl)-2,3,4,7,8,9-hexahydrooxonin

Guidance literature:: prop-1-yne; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.166667h;

(2R,3S,5Z,8R,9S)-[8-benzyloxy-9-benzyloxymethyl-3-(tret-butyldimethylsilyloxy)-2,3,4,7,8,9-hexahydrooxonin-2-yl]methyl trifluoromethanesulfonate; In tetrahydrofuran; at -78 - 24 ℃; for 3h;
DOI:10.1016/j.tet.2006.05.014

Reference yield:

: 876288-77-6
(2R,3S,5Z,8R,9S)-8-benzyloxy-9-benzyloxymethyl-2-hydroxymethyl-2,3,4,7,8,9-hexahydrooxonin-3-ol

: 876288-82-3
(2R,3S,5Z,8R,9S)-3-benzyloxy-2-benzyloxymethyl-8-(tret-butyldimethylsilyloxy)-9-(but-2'-ynyl)-2,3,4,7,8,9-hexahydrooxonin

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 °C

2.1: 17.5 mg / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 - 0 °C

3.1: BuLi / tetrahydrofuran / 0.17 h / -78 °C

3.2: 99 percent / tetrahydrofuran / 3 h / -78 - 24 °C

With 2,6-dimethylpyridine; n-butyllithium; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2006.05.014

Reference yield:

: 876288-76-5
(1R,3S,4R,6Z,9S,11S)-4-benzyloxy-3-benzyloxymethyl-11-phenyl-2,10,12-trioxabicyclo[7.4.0]tridecan-6-ene

: 876288-82-3
(2R,3S,5Z,8R,9S)-3-benzyloxy-2-benzyloxymethyl-8-(tret-butyldimethylsilyloxy)-9-(but-2'-ynyl)-2,3,4,7,8,9-hexahydrooxonin

Guidance literature:: Multi-step reaction with 4 steps

1.1: 98 percent / aq. HCl / tetrahydrofuran / 21 h / 25 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 °C

3.1: 17.5 mg / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 - 0 °C

4.1: BuLi / tetrahydrofuran / 0.17 h / -78 °C

4.2: 99 percent / tetrahydrofuran / 3 h / -78 - 24 °C

With 2,6-dimethylpyridine; hydrogenchloride; n-butyllithium; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2006.05.014