Triisopropyl-((2R,4aR,6S,7R,8aS)-6-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane

Base Information

• Chemical Name: Triisopropyl-((2R,4aR,6S,7R,8aS)-6-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane
• CAS No.: 438002-74-5
• Molecular Formula: C₂₅H₄₀O₄Si
• Molecular Weight: 432.676
• Mol file: 438002-74-5.mol

Synonyms:Triisopropyl-((2R,4aR,6S,7R,8aS)-6-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane

Chemical Property of Triisopropyl-((2R,4aR,6S,7R,8aS)-6-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Triisopropyl-((2R,4aR,6S,7R,8aS)-6-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane

There total 1 articles about Triisopropyl-((2R,4aR,6S,7R,8aS)-6-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane 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:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + (2R,4aR,6S,7R,8aS)-6-Methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (131310-61-7) → Triisopropyl-((2R,4aR,6S,7R,8aS)-6-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane (438002-74-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4039(98)02606-9

Reference yield:

Triisopropyl-((2R,4aR,6S,7R,8aS)-6-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane (438002-74-5) → C41H50O7

Guidance literature:

Multi-step reaction with 22 steps

1.1: p-toluenesulfonic acid hydrate / methanol; CH₂Cl₂ / 19.5 h / 20 °C

2.1: NaH / dimethylformamide / 0.25 h / 20 °C

2.2: 35.53 g / dimethylformamide / 16 h / 20 °C

3.1: 5.53 g / aq. OsO₄; N-methylmorpholine N-oxide / acetone / 19 h / 20 °C

4.1: NaIO₄ / tetrahydrofuran; H₂O / 9 h / 20 °C

5.1: 5.24 g / MgBr₂*Et₂O / CH₂Cl₂ / 2 h / -78 - 20 °C

6.1: NaH / dimethylformamide / 0.5 h / 20 °C

6.2: 100 percent / dimethylformamide / 4.5 h / 0 °C

7.1: osmiumm tetraxide; N-methylmorpholine N-oxide / acetone; H₂O / 9 h / 20 °C

8.1: NaIO₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

9.1: 1.33 g / Sc(OTf)3 / benzene / 20 °C

10.1: 70 percent / CH₂Cl₂; hexane / 2 h / 20 °C

11.1: i-Pr₂NEt / CH₂Cl₂ / 20 °C

12.1: TBAF / tetrahydrofuran / 20 °C

13.1: N-methylmorpholine / CH₂Cl₂ / 20 °C

14.1: 76 percent / n-Bu₃SnH; AIBN / toluene / 80 °C

15.1: DIBALH / CH₂Cl₂; toluene / 1 h / -78 °C

16.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 0 °C

16.2: 24.5 mg / tetrahydrofuran / 0.5 h / 0 °C

17.1: 83 percent / Me₂S; BF₃*Et₂O / CH₂Cl₂ / 1 h / 20 °C

18.1: 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

19.1: n-BuLi; HMPA / tetrahydrofuran / 0.33 h / -78 °C

19.2: 9.3 mg / tetrahydrofuran / 20 h / -78 °C

20.1: 90 percent / K₂CO₃ / methanol; tetrahydrofuran / 10 h / 20 °C

21.1: 88 percent / H₂ / Lindlar catalyst / ethyl acetate / 13 h / 20 °C

22.1: 61 percent / (benzylidene)Ru(PCy₃)2Cl₂ / CH₂Cl₂ / 96 h / 35 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; osmium(VIII) oxide; Grubbs catalyst first generation; n-butyllithium; dimethylsulfide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; magnesium bromide; scandium tris(trifluoromethanesulfonate); Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; benzene; 16.2: Wittig reaction;

DOI:10.1021/jo010974p

Reference yield:

Triisopropyl-((2R,4aR,6S,7R,8aS)-6-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane (438002-74-5) → (2R,3S,4aR,6S,7R,9R,9aS)-6-Allyl-7-((2R,3S)-2-allyl-tetrahydro-pyran-3-yloxy)-3,9-bis-benzyloxy-2-benzyloxymethyl-9a-methyl-octahydro-1,5-dioxa-benzocycloheptene (220864-30-2)

Guidance literature:

Multi-step reaction with 21 steps

1.1: p-toluenesulfonic acid hydrate / methanol; CH₂Cl₂ / 19.5 h / 20 °C

2.1: NaH / dimethylformamide / 0.25 h / 20 °C

2.2: 35.53 g / dimethylformamide / 16 h / 20 °C

3.1: 5.53 g / aq. OsO₄; N-methylmorpholine N-oxide / acetone / 19 h / 20 °C

4.1: NaIO₄ / tetrahydrofuran; H₂O / 9 h / 20 °C

5.1: 5.24 g / MgBr₂*Et₂O / CH₂Cl₂ / 2 h / -78 - 20 °C

6.1: NaH / dimethylformamide / 0.5 h / 20 °C

6.2: 100 percent / dimethylformamide / 4.5 h / 0 °C

7.1: osmiumm tetraxide; N-methylmorpholine N-oxide / acetone; H₂O / 9 h / 20 °C

8.1: NaIO₄ / tetrahydrofuran; H₂O / 1 h / 20 °C

9.1: 1.33 g / Sc(OTf)3 / benzene / 20 °C

10.1: 70 percent / CH₂Cl₂; hexane / 2 h / 20 °C

11.1: i-Pr₂NEt / CH₂Cl₂ / 20 °C

12.1: TBAF / tetrahydrofuran / 20 °C

13.1: N-methylmorpholine / CH₂Cl₂ / 20 °C

14.1: 76 percent / n-Bu₃SnH; AIBN / toluene / 80 °C

15.1: DIBALH / CH₂Cl₂; toluene / 1 h / -78 °C

16.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / 0 °C

16.2: 24.5 mg / tetrahydrofuran / 0.5 h / 0 °C

17.1: 83 percent / Me₂S; BF₃*Et₂O / CH₂Cl₂ / 1 h / 20 °C

18.1: 2,6-lutidine / CH₂Cl₂ / 1 h / -78 °C

19.1: n-BuLi; HMPA / tetrahydrofuran / 0.33 h / -78 °C

19.2: 9.3 mg / tetrahydrofuran / 20 h / -78 °C

20.1: 90 percent / K₂CO₃ / methanol; tetrahydrofuran / 10 h / 20 °C

21.1: 88 percent / H₂ / Lindlar catalyst / ethyl acetate / 13 h / 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; osmium(VIII) oxide; n-butyllithium; dimethylsulfide; 2,2'-azobis(isobutyronitrile); boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; magnesium bromide; scandium tris(trifluoromethanesulfonate); Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; benzene; 16.2: Wittig reaction;

DOI:10.1021/jo010974p

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

(2R,4aR,6S,7R,8aS)-6-Methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Downstream raw materials:

((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-2-vinyl-tetrahydro-pyran-3-yloxy)-triisopropyl-silane

(2R,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-carbaldehyde

(R)-1-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol

(R)-3-Benzyloxy-3-((2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-propionaldehyde