(4R,5S)-5-Benzyloxy-4-isopropyl-2,2-dimethyl-[1,3]dioxane

Base Information

• Chemical Name: (4R,5S)-5-Benzyloxy-4-isopropyl-2,2-dimethyl-[1,3]dioxane
• CAS No.: 113778-80-6
• Molecular Formula: C₁₆H₂₄O₃
• Molecular Weight: 264.365
• Mol file: 113778-80-6.mol

Synonyms:(4R,5S)-5-Benzyloxy-4-isopropyl-2,2-dimethyl-[1,3]dioxane

Chemical Property of (4R,5S)-5-Benzyloxy-4-isopropyl-2,2-dimethyl-[1,3]dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-5-Benzyloxy-4-isopropyl-2,2-dimethyl-[1,3]dioxane

There total 5 articles about (4R,5S)-5-Benzyloxy-4-isopropyl-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:

1-hydroxy-4-methyl-2-(phenylmethoxy)-3-pentanone (113778-44-2) → (4R,5S)-5-Benzyloxy-4-isopropyl-2,2-dimethyl-[1,3]dioxane (113778-80-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / tetramethylammonium triacetoxyborohydride / acetonitrile; acetic acid / -40 deg C, 12 h. then room temp., 1 h.

2: p-toluenesulfonic acid / 3 h

With tetramethylammonium triacetoxyborohydride; toluene-4-sulfonic acid; In acetic acid; acetonitrile;

DOI:10.1021/ja00219a035

Reference yield:

2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentan-3-one (113778-82-8) → (4R,5S)-5-Benzyloxy-4-isopropyl-2,2-dimethyl-[1,3]dioxane (113778-80-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / HF-pyridine complex / acetonitrile / 2 h / 0 °C

2: 76 percent / tetramethylammonium triacetoxyborohydride / acetonitrile; acetic acid / -40 deg C, 12 h. then room temp., 1 h.

3: p-toluenesulfonic acid / 3 h

With pyridine hydrogenfluoride; tetramethylammonium triacetoxyborohydride; toluene-4-sulfonic acid; In acetic acid; acetonitrile;

DOI:10.1021/ja00219a035

Reference yield:

4-methyl-2-(phenylmethoxy)-1,3-pentanediol (113778-42-0,113778-43-1,139561-11-8) → (4R,5S)-5-Benzyloxy-4-isopropyl-2,2-dimethyl-[1,3]dioxane (113778-80-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) triethylamine, DMAP; 2.) pyridinium dichromate, molecular sieves (3 Angstroem) / 1.) dichloromethane, room temp., 12 h.; 2.) dichloromethane, acetic acid, room temp., 2 h.

2: 94 percent / HF-pyridine complex / acetonitrile / 2 h / 0 °C

3: 76 percent / tetramethylammonium triacetoxyborohydride / acetonitrile; acetic acid / -40 deg C, 12 h. then room temp., 1 h.

4: p-toluenesulfonic acid / 3 h

With dmap; dipyridinium dichromate; 3 A molecular sieve; pyridine hydrogenfluoride; triethylamine; tetramethylammonium triacetoxyborohydride; toluene-4-sulfonic acid; In acetic acid; acetonitrile;

DOI:10.1021/ja00219a035

upstream raw materials:

(2S^*,3R^*)-4-methyl-2-(phenylmethoxy)-1,3-pentanediol

2,2-dimethoxy-propane

methyl 2-(benzyloxy)acetate

1-hydroxy-4-methyl-2-(phenylmethoxy)-3-pentanone