1,2-O-Isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose

Base Information

• Chemical Name: 1,2-O-Isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose
• CAS No.: 322390-88-5
• Molecular Formula: C₃₀H₃₂O₆
• Molecular Weight: 488.58
• Mol file: 322390-88-5.mol

Synonyms:1,2-O-Isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose

Chemical Property of 1,2-O-Isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-O-Isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose

There total 5 articles about 1,2-O-Isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose 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: 94.0%

trityl chloride (76-83-5) + 1,2-di-O-isopropylidene-3-C-vinyl-β-D-allofuranose (151426-71-0) → 1,2-O-Isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose (322390-88-5)

Guidance literature:

With pyridine; at 20 ℃; for 50h;

DOI:10.1039/b006082h

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → 1,2-O-Isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose (322390-88-5)

Guidance literature:

Multi-step reaction with 3 steps

1: diethyl ether; tetrahydrofuran

2: acetic acid

3: pyridine

With pyridine; acetic acid; In tetrahydrofuran; diethyl ether; 1: Grignard addition;

DOI:10.1081/NCN-100002543

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1,2-O-Isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose (322390-88-5)

Guidance literature:

Multi-step reaction with 4 steps

1: chromium(VI) oxide; acetic anhydride; pyridine / CH₂Cl₂

2: diethyl ether; tetrahydrofuran

3: acetic acid

4: pyridine

With pyridine; chromium(VI) oxide; acetic anhydride; acetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; 2: Grignard addition;

DOI:10.1081/NCN-100002543

upstream raw materials:

trityl chloride

1,2-di-O-isopropylidene-3-C-vinyl-β-D-allofuranose

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

3,5-Di-O-benzyl-1,2-O-isopropylidene-6-O-triphenylmethyl-3-C-vinyl-α-D-allofuranose

(3aR,5R,6R,6aR)-2,2-Dimethyl-5-(2-trityloxy-ethyl)-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol

(1R,2S,3S,4R,5S)-2,5-Bis-benzyloxy-3,4-bis-benzyloxymethyl-2-hydroxymethyl-4-methyl-cyclohexanol

(3aR,4aR,6S,7R,8S,8aR,8bR)-6,8a-Bis-benzyloxy-7,8-bis-benzyloxymethyl-2,2,7-trimethyl-octahydro-benzo[4,5]furo[2,3-d][1,3]dioxole