methyl 4,6-O-benzylidene-3-deoxy-3-C-methylene-α-D-ribo-hexopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-3-deoxy-3-C-methylene-α-D-ribo-hexopyranoside
• CAS No.: 50827-20-8
• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.305
• Mol file: 50827-20-8.mol

Synonyms:methyl 4,6-O-benzylidene-3-deoxy-3-C-methylene-α-D-ribo-hexopyranoside

Chemical Property of methyl 4,6-O-benzylidene-3-deoxy-3-C-methylene-α-D-ribo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,6-O-benzylidene-3-deoxy-3-C-methylene-α-D-ribo-hexopyranoside

There total 5 articles about methyl 4,6-O-benzylidene-3-deoxy-3-C-methylene-α-D-ribo-hexopyranoside 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: 58.0%

methyl 2-O-benzoyl-4,6-O-benzylidene-3-<(trimethylsilyl)methyl>-α-D-allopyranoside (82198-67-2) → methyl 4,6-O-benzylidene-3-deoxy-3-C-methylene-α-D-ribo-hexopyranoside (50827-20-8)

Guidance literature:

With potassium hydride; In tetrahydrofuran; for 4h; Heating;

DOI:10.1021/jo00139a035

Reference yield:

(2R,4aR,6S,7R,8aR)-6-methoxy-8-oxo-2-phenyl-7-phenylcarbonyloxyperhydropyrano[3,2-d][1,3]dioxine (68366-59-6) → methyl 4,6-O-benzylidene-3-deoxy-3-C-methylene-α-D-ribo-hexopyranoside (50827-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Mg, (bromomethyl)trimethylsilane / 1.) anhydrous ether, reflux, 1 h, 2.) toluene, room temperature, 3 h

2: 58 percent / KH / tetrahydrofuran / 4 h / Heating

With (bromomethyl)trimethylsilane; potassium hydride; magnesium; In tetrahydrofuran;

DOI:10.1021/jo00139a035

Reference yield:

→ (2R,4aR,6S,7S,8aS)-6-Methoxy-8-methylene-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (50827-20-8)

Guidance literature:

Benzoat 15a, NaOH;

DOI:10.1016/S0008-6215(00)84454-7

upstream raw materials:

methyl 2-O-benzoyl-4,6-O-benzylidene-3-<(trimethylsilyl)methyl>-α-D-allopyranoside

(2R,4aR,6S,7R,8aR)-6-methoxy-8-oxo-2-phenyl-7-phenylcarbonyloxyperhydropyrano[3,2-d][1,3]dioxine

Downstream raw materials:

(2R,4aR,6S,7R,8R,8aS)-8-((3aR,4S,6S,7R,7aS)-7-Hydroxy-2,2,4-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethyl)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol