<4S-(4β,6β)>-6-ethenyl-4-<<<(1,1-dimethylethyl)diphenylsilyl>oxy>methyl>-2,2-dimethyl-1,3-dioxane

Base Information

• Chemical Name: <4S-(4β,6β)>-6-ethenyl-4-<<<(1,1-dimethylethyl)diphenylsilyl>oxy>methyl>-2,2-dimethyl-1,3-dioxane
• CAS No.: 114861-19-7
• Molecular Formula: C₂₅H₃₄O₃Si
• Molecular Weight: 410.629
• Mol file: 114861-19-7.mol

Synonyms:<4S-(4β,6β)>-6-ethenyl-4-<<<(1,1-dimethylethyl)diphenylsilyl>oxy>methyl>-2,2-dimethyl-1,3-dioxane

Chemical Property of <4S-(4β,6β)>-6-ethenyl-4-<<<(1,1-dimethylethyl)diphenylsilyl>oxy>methyl>-2,2-dimethyl-1,3-dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <4S-(4β,6β)>-6-ethenyl-4-<<<(1,1-dimethylethyl)diphenylsilyl>oxy>methyl>-2,2-dimethyl-1,3-dioxane

There total 11 articles about <4S-(4β,6β)>-6-ethenyl-4-<<<(1,1-dimethylethyl)diphenylsilyl>oxy>methyl>-2,2-dimethyl-1,3-dioxane 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: 90.0%

(2S,4R)-7-<<(1,1-dimethylethyl)diphenylsilyl>oxy>5-hexene-2,4-diol (106862-35-5) + 2,2-dimethoxy-propane (77-76-9) → <4S-(4β,6β)>-6-ethenyl-4-<<<(1,1-dimethylethyl)diphenylsilyl>oxy>methyl>-2,2-dimethyl-1,3-dioxane (114861-19-7)

Guidance literature:

camphor-10-sulfonic acid; at 25 ℃; for 1h;

DOI:10.1021/ja00241a062

Reference yield:

D-xylofuranose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) → <4S-(4β,6β)>-6-ethenyl-4-<<<(1,1-dimethylethyl)diphenylsilyl>oxy>methyl>-2,2-dimethyl-1,3-dioxane (114861-19-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 50 percent / conc. H₂SO₄ / 1.) 25 deg C, 6h, 2.) MeOH, 25 deg C, 2h

2: 96 percent / imidazole / dimethylformamide / 2 h / 0 - 25 °C

3: 94 percent / pyr / DMAP / CH₂Cl₂ / 15 h / 0 - 25 °C

4: 77 percent / n-Bu₃SnH / AlBN / toluene / 1 h / 80 °C

5: 90 percent / BCl₃ / CH₂Cl₂; hexane / 0.17 h / -78 °C

6: 67 percent / NaH / tetrahydrofuran / 4 h / -30 - 25 °C

7: 90 percent / CSA / 1 h / 25 °C

With pyridine; 1H-imidazole; tri-n-butyl-tin hydride; boron trichloride; sodium hydride; dmap; 2,2'-azobis(isobutyronitrile); sulfuric acid; camphor-10-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00241a062

Reference yield:

1,2-O-isopropylidene-α-D-xylose (20031-21-4) → <4S-(4β,6β)>-6-ethenyl-4-<<<(1,1-dimethylethyl)diphenylsilyl>oxy>methyl>-2,2-dimethyl-1,3-dioxane (114861-19-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / imidazole / dimethylformamide / 2 h / 0 - 25 °C

2: 94 percent / pyr / DMAP / CH₂Cl₂ / 15 h / 0 - 25 °C

3: 77 percent / n-Bu₃SnH / AlBN / toluene / 1 h / 80 °C

4: 90 percent / BCl₃ / CH₂Cl₂; hexane / 0.17 h / -78 °C

5: 67 percent / NaH / tetrahydrofuran / 4 h / -30 - 25 °C

6: 90 percent / CSA / 1 h / 25 °C

With pyridine; 1H-imidazole; tri-n-butyl-tin hydride; boron trichloride; sodium hydride; dmap; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00241a062

upstream raw materials:

(2S,4R)-7-<<(1,1-dimethylethyl)diphenylsilyl>oxy>5-hexene-2,4-diol

2,2-dimethoxy-propane

3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

(2S,4R)-5,5-bis(ethylthio)-1,2,4-pentanetriol

Downstream raw materials:

2,3-dideoxy-6-O-<(1,1-dimethylethyl)diphenylsilyl>-3,5-O-(1-methylethylidene)-1-O-(phenylmethyl)-D-erythro-hexitol

3,5-dideoxy-2,4-O-(1-methylethylidene)-6-O-(phenylmethyl)-L-erythro-hexose

2,3-dideoxy-3,5-O-(1-methylethylidene)-1-O-(phenylmethyl)-D-erythro-hexitol

2,3-dideoxy-6-O-<(1,1-dimethylethyl)diphenylsilyl>3,5-O-(1-methylethylidene)-D-erythro-hexitol