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)-propynone

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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)-propynone
CAS No.:240133-67-9
Molecular Formula:C₃₁H₄₇BrO₅Si
Molecular Weight:607.701
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)-propynone

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)-propynone

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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)-propynone

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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)-propynone

There total 20 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)-propynone 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: 89.0%

: 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

: 240133-67-9
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)-propynone

Guidance literature:: With manganese(IV) oxide; In hexane; at 20 ℃; for 7h;
DOI:10.1021/ja000001r DOI:10.1021/ol990648k

Reference yield:

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

: 240133-67-9
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)-propynone

Guidance literature:: Multi-step reaction with 13 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

13.1: 89 percent / MnO₂ / hexane / 7 h / 20 °C

With 1H-imidazole; chromium dichloride; titanium(IV) isopropylate; tert.-butylhydroperoxide; manganese(IV) oxide; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; decane; hexane; 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

: 240133-67-9
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)-propynone

Guidance literature:: Multi-step reaction with 13 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

13.1: 89 percent / MnO₂ / hexane / 7 h / 20 °C

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