(4S,5S,6S)-4-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-6-vinyl-[1,3]dioxane

Base Information

• Chemical Name: (4S,5S,6S)-4-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-6-vinyl-[1,3]dioxane
• CAS No.: 149916-87-0
• Molecular Formula: C₁₈H₂₆O₃
• Molecular Weight: 290.403
• Mol file: 149916-87-0.mol

Synonyms:

Chemical Property of (4S,5S,6S)-4-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-6-vinyl-[1,3]dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S,6S)-4-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-6-vinyl-[1,3]dioxane

There total 12 articles about (4S,5S,6S)-4-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-6-vinyl-[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: 85.0%

(3S,4S,5S)-7-Benzyloxy-4-methyl-hept-1-ene-3,5-diol (128684-70-8) + 2,2-dimethoxy-propane (77-76-9) → (4S,5S,6S)-4-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-6-vinyl-[1,3]dioxane (149916-87-0)

Guidance literature:

With camphor-10-sulfonic acid;

DOI:10.1016/S0040-4039(00)60495-1

Reference yield:

3-benzyloxypropan-1-ol (4799-68-2) → (4S,5S,6S)-4-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-6-vinyl-[1,3]dioxane (149916-87-0)

Guidance literature:

Multi-step reaction with 11 steps

1: PCC, NaOAc / CH₂Cl₂

2: benzene

3: DIBAL-H / CH₂Cl₂ / -10 °C

4: (+)-DET, titanium tetraisopropoxide (TIP), tertiary butylhydroperoxide (TBHP), molecular sieves / CH₂Cl₂ / -25 °C

5: CrO₃, pyridine, molecular sieves, celite / CH₂Cl₂

6: benzene

7: 65 percent / H₂O / 1,2-dichloro-ethane / -30 °C

8: 85 percent / DIBAL-H / CH₂Cl₂ / -10 °C

9: (-)-DIPT, TBHP, molecular sieves / CH₂Cl₂ / -25 °C

10: 70 percent / titanocene dichloride, zinc, ZnCl₂ / tetrahydrofuran

11: 85 percent / camphor sulfonic acid (CSA)

With pyridine; chromium(VI) oxide; titanium(IV) isopropylate; tert.-butylhydroperoxide; molecular sieve; diethyl (2R,3R)-tartrate; Celite; titanocene dichloride; camphor-10-sulfonic acid; water; sodium acetate; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; pyridinium chlorochromate; zinc(II) chloride; zinc; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; benzene;

DOI:10.1016/S0040-4039(00)60495-1

Reference yield:

ethyl (2E)-5-(benzyloxy)pent-2-enoate (70542-83-5) → (4S,5S,6S)-4-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-6-vinyl-[1,3]dioxane (149916-87-0)

Guidance literature:

Multi-step reaction with 9 steps

1: DIBAL-H / CH₂Cl₂ / -10 °C

2: (+)-DET, titanium tetraisopropoxide (TIP), tertiary butylhydroperoxide (TBHP), molecular sieves / CH₂Cl₂ / -25 °C

3: CrO₃, pyridine, molecular sieves, celite / CH₂Cl₂

4: benzene

5: 65 percent / H₂O / 1,2-dichloro-ethane / -30 °C

6: 85 percent / DIBAL-H / CH₂Cl₂ / -10 °C

7: (-)-DIPT, TBHP, molecular sieves / CH₂Cl₂ / -25 °C

8: 70 percent / titanocene dichloride, zinc, ZnCl₂ / tetrahydrofuran

9: 85 percent / camphor sulfonic acid (CSA)

With pyridine; chromium(VI) oxide; titanium(IV) isopropylate; tert.-butylhydroperoxide; molecular sieve; diethyl (2R,3R)-tartrate; Celite; titanocene dichloride; camphor-10-sulfonic acid; water; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; zinc(II) chloride; zinc; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; benzene;

DOI:10.1016/S0040-4039(00)60495-1

upstream raw materials:

(3S,4S,5S)-7-Benzyloxy-4-methyl-hept-1-ene-3,5-diol

2,2-dimethoxy-propane

3-benzyloxypropan-1-ol

ethyl (2E)-5-(benzyloxy)pent-2-enoate

Downstream raw materials:

1-[(4R,5S,6S)-6-(2-Benzyloxy-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-ethanone