3-C-Methyl-1,2-O-(1-Methylethylidene)-5-benzoate-alpha-D-ribofuranose

Base Information

• Chemical Name: 3-C-Methyl-1,2-O-(1-Methylethylidene)-5-benzoate-alpha-D-ribofuranose
• CAS No.: 16831-81-5
• Molecular Formula: C16H20O6
• Molecular Weight: 308.331
• Mol file: 16831-81-5.mol

Synonyms:3-C-Methyl-1,2-O-(1-Methylethylidene)-5-benzoate-alpha-D-ribofuranose;3-C-Methyl-1,2-O-(1-methylethylidene)-alpha-D-ribofuranose 5-benzoate

Chemical Property of 3-C-Methyl-1,2-O-(1-Methylethylidene)-5-benzoate-alpha-D-ribofuranose

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-C-Methyl-1,2-O-(1-Methylethylidene)-5-benzoate-alpha-D-ribofuranose

There total 10 articles about 3-C-Methyl-1,2-O-(1-Methylethylidene)-5-benzoate-alpha-D-ribofuranose 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: 85.0%

(3aR,5R,6R,6aR)-5-(hydroxymethyl)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (24467-33-2) + benzoyl chloride (98-88-4) → ((3aR,5R,6R,6aR)-6-hydroxy-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (16831-81-5)

Guidance literature:

With pyridine; at 0 ℃; for 16h;

DOI:10.1016/0008-6215(83)88357-8

Reference yield: 80.0%

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0) + methylmagnesium bromide (75-16-1) → ((3aR,5R,6R,6aR)-6-hydroxy-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (16831-81-5)

Guidance literature:

In diethyl ether;

DOI:10.1080/15257770701521730

Reference yield:

5-O-benzoyl-α-D-xylofuranose (6022-96-4) → ((3aR,5R,6R,6aR)-6-hydroxy-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (16831-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine dichromate; Ac₂O / CH₂Cl₂

2: CH₂Cl₂

With pyridinium dichromate; acetic anhydride; In dichloromethane;

DOI:10.1021/jm048944c

upstream raw materials:

(3aR,5R,6R,6aR)-5-(hydroxymethyl)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

benzoyl chloride

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose

methylmagnesium bromide

Downstream raw materials:

((2R,3S,4R,5S)-3,4,5-trihydroxy-3-methyltetrahydrofuran-2-yl)methyl benzoate

(3R,4R,5R)-5-((benzoyloxy)methyl)-4-methyltetrahydrofuran-2,3,4-triyl triacetate

5-O-benzoyl-3-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-erythro-pentofuranose