3-((2S,3R,6R)-6-Benzyloxymethyl-2-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl)-1-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

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Chemical Name:3-((2S,3R,6R)-6-Benzyloxymethyl-2-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl)-1-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol
CAS No.:240133-66-8
Molecular Formula:C₃₁H₄₉BrO₅Si
Molecular Weight:609.717
Hs Code.:

3-((2S,3R,6R)-6-Benzyloxymethyl-2-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl)-1-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

Synonyms:3-((2S,3R,6R)-6-Benzyloxymethyl-2-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl)-1-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

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Chemical Property of 3-((2S,3R,6R)-6-Benzyloxymethyl-2-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl)-1-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

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Technology Process of 3-((2S,3R,6R)-6-Benzyloxymethyl-2-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl)-1-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

There total 18 articles about 3-((2S,3R,6R)-6-Benzyloxymethyl-2-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl)-1-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-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: 75.0%

: 240133-55-5
5-bromo-2,6,6-trimethyl-(5R)-tetrahydropyran-2-carbaldehyde

: 240133-56-6
((2S,3R,6R)-6-Benzyloxymethyl-2-bromoethynyl-2-methyl-tetrahydro-pyran-3-yloxy)-triethyl-silane

: 240133-66-8
3-((2S,3R,6R)-6-Benzyloxymethyl-2-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl)-1-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

Guidance literature:: With chromium dichloride; nickel dichloride; In N,N-dimethyl-formamide; at 20 ℃; for 5h;
DOI:10.1021/ja000001r

Reference yield:

: 52813-63-5
(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

: 240133-66-8
3-((2S,3R,6R)-6-Benzyloxymethyl-2-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl)-1-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 63 percent / TfOH / CH₂Cl₂; pentane / 30 h / 0 °C

2.1: DIBAL / toluene / 1 h / -78 °C

3.1: 2.04 g / benzene / 2 h / Heating

4.1: 95 percent / imidazole / dimethylformamide / 3 h / 20 °C

5.1: 72 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 86 percent / (-)-D-diethyl tartrate; Ti(O-i-Pr)4; tert-butylhydroperoxide / CH₂Cl₂; decane / 5 h / -23 °C

7.1: 92 percent / Et₃N; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 4 h / 0 °C

8.1: PPh₃ / CH₂Cl₂ / 0.33 h / 0 °C

8.2: 91 percent / Et₃N / CH₂Cl₂ / 0.75 h / -78 °C

9.1: 88 percent / TBAF / tetrahydrofuran / 9 h / 20 °C

10.1: 91 percent / BF₃*OEt₂ / CH₂Cl₂ / 6.5 h / -78 - -10 °C

11.1: 85 percent / imidazole / dimethylformamide / 6 h / 20 °C

12.1: 66 percent / CrCl₂ / dimethylformamide / 20 h / 20 °C

With 1H-imidazole; chromium dichloride; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; decane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; pentane; benzene; 6.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol990648k

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 240133-66-8
3-((2S,3R,6R)-6-Benzyloxymethyl-2-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-yl)-1-((2S,5R)-5-bromo-2,6,6-trimethyl-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 63 percent / TfOH / CH₂Cl₂; pentane / 30 h / 0 °C

2.1: DIBAL / toluene / 1 h / -78 °C

3.1: 2.04 g / benzene / 2 h / Heating

4.1: 95 percent / imidazole / dimethylformamide / 3 h / 20 °C

5.1: 72 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 86 percent / (-)-D-diethyl tartrate; Ti(O-i-Pr)4; tert-butylhydroperoxide / CH₂Cl₂; decane / 5 h / -23 °C

7.1: 92 percent / Et₃N; SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 4 h / 0 °C

8.1: PPh₃ / CH₂Cl₂ / 0.33 h / 0 °C

8.2: 91 percent / Et₃N / CH₂Cl₂ / 0.75 h / -78 °C

9.1: 88 percent / TBAF / tetrahydrofuran / 9 h / 20 °C

10.1: 91 percent / BF₃*OEt₂ / CH₂Cl₂ / 6.5 h / -78 - -10 °C

11.1: 85 percent / imidazole / dimethylformamide / 6 h / 20 °C

12.1: 66 percent / CrCl₂ / dimethylformamide / 20 h / 20 °C

With 1H-imidazole; chromium dichloride; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; decane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; pentane; benzene; 6.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol990648k