tert-Butyl-dimethyl-[(2R,4S,5R)-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-yloxy]-silane

Base Information

• Chemical Name: tert-Butyl-dimethyl-[(2R,4S,5R)-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-yloxy]-silane
• CAS No.: 131310-59-3
• Molecular Formula: C₂₂H₃₄O₄Si
• Molecular Weight: 390.595

Synonyms:tert-Butyl-dimethyl-[(2R,4S,5R)-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-yloxy]-silane

Chemical Property of tert-Butyl-dimethyl-[(2R,4S,5R)-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-yloxy]-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-dimethyl-[(2R,4S,5R)-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-yloxy]-silane

There total 8 articles about tert-Butyl-dimethyl-[(2R,4S,5R)-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-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: 88.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (2S,3R)-3-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl]-2-methyl-oxirane-2-carbaldehyde (131310-58-2) → tert-Butyl-dimethyl-[(2R,4S,5R)-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-yloxy]-silane (131310-59-3)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1016/S0040-4020(01)85579-4

Reference yield:

2-deoxy-D-ribose (22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7) → tert-Butyl-dimethyl-[(2R,4S,5R)-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-yloxy]-silane (131310-59-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / tetrahydrofuran / 3 h / Heating

2: 96 percent / camphorsulfonic acid / CH₂Cl₂ / 12 h / 25 °C

3: 98 percent / imidazole / dimethylformamide / 5 h / 25 °C

4: 98 percent / DIBAL / CH₂Cl₂ / 0.67 h / -78 °C

5: 1.) diethyl-D-tartrate, titanium(IV) isopropoxide, 2.) tert-butylhydroperoxide / 1.) CH₂Cl₂, -27 deg C, 30 min, 2.) 2,2,4-trimethylpentane, -20 deg C, 14 h

6: 94 percent / SO₃*pyridine, NEt₃ / CH₂Cl₂; dimethylsulfoxide / 3.5 h / 0 °C

7: 88 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.25 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)85579-4

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → tert-Butyl-dimethyl-[(2R,4S,5R)-4-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-[1,3]dioxan-5-yloxy]-silane (131310-59-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / camphorsulfonic acid / CH₂Cl₂ / 12 h / 25 °C

2: 98 percent / imidazole / dimethylformamide / 5 h / 25 °C

3: 98 percent / DIBAL / CH₂Cl₂ / 0.67 h / -78 °C

4: 1.) diethyl-D-tartrate, titanium(IV) isopropoxide, 2.) tert-butylhydroperoxide / 1.) CH₂Cl₂, -27 deg C, 30 min, 2.) 2,2,4-trimethylpentane, -20 deg C, 14 h

5: 94 percent / SO₃*pyridine, NEt₃ / CH₂Cl₂; dimethylsulfoxide / 3.5 h / 0 °C

6: 88 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.25 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)85579-4

upstream raw materials:

Methyltriphenylphosphonium bromide

(2S,3R)-3-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-ylmethyl]-2-methyl-oxirane-2-carbaldehyde

2-deoxy-D-ribose

benzaldehyde dimethyl acetal

Downstream raw materials:

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

2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

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

[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-acetaldehyde

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