(1R)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-trityloxy-ethanol

Base Information

• Chemical Name: (1R)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-trityloxy-ethanol
• CAS No.: 95666-80-1
• Molecular Formula: C28H30O4
• Molecular Weight: 430.544
• Mol file: 95666-80-1.mol

Synonyms:D-ribo-Hex-1-enitol, 1,2-dideoxy-3,4-O-(1-Methylethylidene)-6-O-(triphenylMethyl)-;D-ribo-Hex-1-enitol, 1,2-dideoxy-3,4-O-(1-Methylethylidene)-6-O-(triphenylMethyl)-4

Chemical Property of (1R)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-trityloxy-ethanol

Chemical Property:

• Vapor Pressure: 7.72E-13mmHg at 25°C
• Boiling Point: 547.9°C at 760 mmHg
• Flash Point: 285.2°C
• PSA: 47.92000
• Density: 1.151g/cm³
• LogP: 5.06210

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-trityloxy-ethanol

There total 4 articles about (1R)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-trityloxy-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: 96.0%

2,3-O-isopropylidene-5-O-trityl-D-ribofuranose (54503-64-9,54503-65-0) + Methylenetriphenylphosphorane (19493-09-5) → (1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(triphenylmethyloxy)ethan-1-ol (95666-80-1)

Guidance literature:

In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/S0040-4039(01)81725-1

Reference yield: 93.0%

2,3-O-isopropylidene-5-O-trityl-D-ribofuranose (54503-64-9,54503-65-0) + Methyltriphenylphosphonium bromide (1779-49-3) → (1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(triphenylmethyloxy)ethan-1-ol (95666-80-1)

Guidance literature:

With sodium hydride; In tetrahydrofuran; dimethyl sulfoxide; at -10 - 60 ℃; for 4h;

DOI:10.1021/jo050987t

Reference yield:

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) → (1R)-(-)-1-[(4R,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]-2-(triphenylmethyloxy)ethan-1-ol (95666-80-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / pyridine / 20 h / 20 °C

2.1: potassium tert-butoxide / tetrahydrofuran / 0 - 20 °C

2.2: 82 percent / tetrahydrofuran / 7 h / 0 - 20 °C

With pyridine; potassium tert-butylate; In tetrahydrofuran; 2.2: Wittig reaction;

DOI:10.1021/jo0356762

upstream raw materials:

2,3-O-isopropylidene-5-O-trityl-D-ribofuranose

Methylenetriphenylphosphorane

Methyltriphenylphosphonium bromide

2,3-O-isopropylidene-D-ribofuranose

Downstream raw materials:

2-{1-[(R)-1-((4S,5S)-2,2-Dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-2-trityloxy-ethoxy]-allyloxy}-tetrahydro-pyran

(4S,5S)-4-((R)-1-Allyloxy-2-trityloxy-ethyl)-2,2-dimethyl-5-vinyl-[1,3]dioxolane

diethyl (2,3-isopropylidene-5-trityl-α-D-ribofuranosyl)-methanephosphonate

(3aR,4S,6R,6aR)-4-Iodomethyl-2,2-dimethyl-6-trityloxymethyl-tetrahydro-furo[3,4-d][1,3]dioxole