methyl 2,3-O-(internal carbonate)-4,6-O-(phenylmethylene)-α-D-allopyranoside

Base Information

• Chemical Name: methyl 2,3-O-(internal carbonate)-4,6-O-(phenylmethylene)-α-D-allopyranoside
• CAS No.: 129263-19-0
• Molecular Formula: C₁₅H₁₆O₇
• Molecular Weight: 308.288
• Mol file: 129263-19-0.mol

Synonyms:methyl 2,3-O-(internal carbonate)-4,6-O-(phenylmethylene)-α-D-allopyranoside

Chemical Property of methyl 2,3-O-(internal carbonate)-4,6-O-(phenylmethylene)-α-D-allopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3-O-(internal carbonate)-4,6-O-(phenylmethylene)-α-D-allopyranoside

There total 5 articles about methyl 2,3-O-(internal carbonate)-4,6-O-(phenylmethylene)-α-D-allopyranoside 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: 81.0%

methyl 4,6-O-benzylidene-α-D-allopyranoside (79549-74-9) + dichloromethylenedimethyliminium chloride (33842-02-3,529510-96-1) → methyl 2,3-O-carbonyl-4,6-O-benzylidene-α-D-alloside (14419-73-9,18390-85-7,19773-96-7,56155-88-5,59332-71-7,74560-57-9,74560-59-1,74984-87-5,82079-41-2,129263-19-0,129263-20-3)

Guidance literature:

With pyridine; In dichloromethane; at 25 ℃; for 0.5h;

Reference yield: 7.0%

methyl 4,6-O-benzylidene-α-D-allopyranoside (79549-74-9) + dichloromethylenedimethyliminium chloride (33842-02-3,529510-96-1) → methyl 2,3-O-carbonyl-4,6-O-benzylidene-α-D-alloside (14419-73-9,18390-85-7,19773-96-7,56155-88-5,59332-71-7,74560-57-9,74560-59-1,74984-87-5,82079-41-2,129263-19-0,129263-20-3) + methyl 4,6-O-benzylidene-3-O-(N,N-dimethylcarbamoyl)-α-D-alloside (82039-67-6,82877-73-4)

Guidance literature:

With triethylamine; In dichloromethane; at 25 ℃; for 0.5h;

Reference yield:

methyl 2-O-(benzoylcarbamyl)-4,6-O-(phenylmethylene)-3-O-<(trifluoromethyl)sulfonyl>-α-D-glucopyranoside (129217-35-2) → methyl 2,3-O-(internal carbonate)-4,6-O-(phenylmethylene)-α-D-allopyranoside (129263-19-0) + N-[(3aR,4S,5aR,8R,9aR,9bR)-4-Methoxy-8-phenyl-hexahydro-[1,3]dioxolo[4',5':4,5]pyrano[3,2-d][1,3]dioxin-(2Z)-ylidene]-benzamide (129217-36-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 ℃; for 12h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00309a013

upstream raw materials:

methyl 2-O-(benzoylcarbamyl)-4,6-O-(phenylmethylene)-3-O-<(trifluoromethyl)sulfonyl>-α-D-glucopyranoside

4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside

methyl 4,6-O-benzylidene-α-D-allopyranoside

dichloromethylenedimethyliminium chloride

Downstream raw materials:

methyl 4,6-O-benzylidene-α-D-allopyranoside