(4S-cis)-<6-(iodomethyl)-2,2-dimethyl-1,3-dioxan-4-yl>ethanol

Base Information

• Chemical Name: (4S-cis)-<6-(iodomethyl)-2,2-dimethyl-1,3-dioxan-4-yl>ethanol
• CAS No.: 125975-00-0
• Molecular Formula: C₉H₁₇IO₃
• Molecular Weight: 300.137
• Mol file: 125975-00-0.mol

Synonyms:(4S-cis)-<6-(iodomethyl)-2,2-dimethyl-1,3-dioxan-4-yl>ethanol

Chemical Property of (4S-cis)-<6-(iodomethyl)-2,2-dimethyl-1,3-dioxan-4-yl>ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S-cis)-<6-(iodomethyl)-2,2-dimethyl-1,3-dioxan-4-yl>ethanol

There total 1 articles about (4S-cis)-<6-(iodomethyl)-2,2-dimethyl-1,3-dioxan-4-yl>ethanol 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: 39.0%

4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-iodomethyl-[1,3]dioxan-2-one (116996-55-5,126060-84-2) + acetone (67-64-1) → (4S-cis)-<6-(iodomethyl)-2,2-dimethyl-1,3-dioxan-4-yl>ethanol (125975-00-0) + (4S-cis)-(1,1-dimethylethyl)<2-<6-(iodomethyl)-2,2-dimethyl-1,3-dioxan-4-yl>ethoxy>diphenylsilane (116996-29-3)

Guidance literature:

With toluene-4-sulfonic acid; for 91h; Ambient temperature;

DOI:10.1021/ja00164a024

Reference yield:

(4S-cis)-<6-(iodomethyl)-2,2-dimethyl-1,3-dioxan-4-yl>ethanol (125975-00-0) → 3-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-((1R,2S,5S)-5-hydroxy-2-methyl-cyclohex-3-enyl)-propionaldehyde (125975-01-1,126060-28-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 °C

2: 1.) LDA / 1.) THF, -78 deg C, 1.25 h, 2.) THF, hexamethylphosphoric triamide (HMPA), from -78 deg C to RT, overnight

3: 90 percent / 1 M diisobutylaluminium hydride / CH₂Cl₂ / 1.5 h / -78 °C

With dmap; diisobutylaluminium hydride; triethylamine; lithium diisopropyl amide; In dichloromethane;

DOI:10.1021/ja00164a024

Reference yield:

(4S-cis)-<6-(iodomethyl)-2,2-dimethyl-1,3-dioxan-4-yl>ethanol (125975-00-0) → <1S-<1α,4α-(4S*,6R*),5α,6β>>-4-<<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>methyl>-6-methyl-2-oxabicyclo<3.3.1>non-7-en-3-one (116996-30-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 °C

2: 1.) LDA / 1.) THF, -78 deg C, 1.25 h, 2.) THF, hexamethylphosphoric triamide (HMPA), from -78 deg C to RT, overnight

With dmap; triethylamine; lithium diisopropyl amide; In dichloromethane;

DOI:10.1021/ja00164a024

upstream raw materials:

4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-iodomethyl-[1,3]dioxan-2-one

acetone

Downstream raw materials:

3-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-((1R,2S,5S)-5-hydroxy-2-methyl-cyclohex-3-enyl)-propionaldehyde

<1S-<1α,4α-(4S^*,6R^*),5α,6β>>-4-<<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>methyl>-6-methyl-2-oxabicyclo<3.3.1>non-7-en-3-one