2,4,5-tri-O-acetyl-3-O-allyl-5,6-dideoxy-1-C-phenyl-hex-1-enitol

Base Information

• Chemical Name: 2,4,5-tri-O-acetyl-3-O-allyl-5,6-dideoxy-1-C-phenyl-hex-1-enitol
• CAS No.: 844866-74-6
• Molecular Formula: C₂₁H₂₆O₇
• Molecular Weight: 390.433
• Mol file: 844866-74-6.mol

Synonyms:2,4,5-tri-O-acetyl-3-O-allyl-5,6-dideoxy-1-C-phenyl-hex-1-enitol

Chemical Property of 2,4,5-tri-O-acetyl-3-O-allyl-5,6-dideoxy-1-C-phenyl-hex-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4,5-tri-O-acetyl-3-O-allyl-5,6-dideoxy-1-C-phenyl-hex-1-enitol

There total 4 articles about 2,4,5-tri-O-acetyl-3-O-allyl-5,6-dideoxy-1-C-phenyl-hex-1-enitol 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: 49.0%

acetic anhydride (108-24-7) + phenylmagnesium bromide + (3R,4R,5R)-4-Allyloxy-5-vinyl-tetrahydro-furan-2,3-diol → 2,4,5-tri-O-acetyl-3-O-allyl-5,6-dideoxy-1-C-phenyl-hex-1-enitol (844866-74-6)

Guidance literature:

phenylmagnesium bromide; (3R,4R,5R)-4-Allyloxy-5-vinyl-tetrahydro-furan-2,3-diol; In tetrahydrofuran; at 0 - 20 ℃; for 30h;

acetic anhydride; With dmap; In pyridine; for 24h;

DOI:10.1016/S0040-4039(02)01048-1

Reference yield:

(3R,5R,6S,6R)(6-allyloxy)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole (226919-74-0) → 2,4,5-tri-O-acetyl-3-O-allyl-5,6-dideoxy-1-C-phenyl-hex-1-enitol (844866-74-6)

Guidance literature:

Multi-step reaction with 3 steps

1: AcOH / H₂O / 12 h / Heating

2: 0.36 g / tetrahydrofuran / 32 h / 0 - 20 °C

3: 0.35 g / Et₃N; DMAP / 24 h / 20 °C

With dmap; acetic acid; triethylamine; In tetrahydrofuran; water;

DOI:10.1016/j.tet.2006.09.016

Reference yield:

(3R,4R,5R)-4-Allyloxy-5-vinyl-tetrahydro-furan-2,3-diol → 2,4,5-tri-O-acetyl-3-O-allyl-5,6-dideoxy-1-C-phenyl-hex-1-enitol (844866-74-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.36 g / tetrahydrofuran / 32 h / 0 - 20 °C

2: 0.35 g / Et₃N; DMAP / 24 h / 20 °C

With dmap; triethylamine; In tetrahydrofuran;

DOI:10.1016/j.tet.2006.09.016

upstream raw materials:

acetic anhydride

(3R,5R,6S,6R)(6-allyloxy)-2,2-dimethyl-5-vinyltetrahydrofuro[2,3-d][1,3]dioxole

Downstream raw materials:

1,2,4-tri-O-acetyl-3,7-anhydro-5,6-dideoxy-1-C-phenyl-hept-5-enitol