methyl 2,4-anhydro-(R)-3,5-O-benzylidene-L-rhamnonate

Base Information

• Chemical Name: methyl 2,4-anhydro-(R)-3,5-O-benzylidene-L-rhamnonate
• CAS No.: 322726-61-4
• Molecular Formula: C₁₄H₁₆O₅
• Molecular Weight: 264.278
• Mol file: 322726-61-4.mol

Synonyms:methyl 2,4-anhydro-(R)-3,5-O-benzylidene-L-rhamnonate

Chemical Property of methyl 2,4-anhydro-(R)-3,5-O-benzylidene-L-rhamnonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,4-anhydro-(R)-3,5-O-benzylidene-L-rhamnonate

There total 9 articles about methyl 2,4-anhydro-(R)-3,5-O-benzylidene-L-rhamnonate 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: 89.0%

methanol (67-56-1) + (R)-3,5-O-benzylidene-2-O-trifluoromethanesulfonyl-L-rhamnono-1,4-lactone (322726-62-5) → methyl 2,4-anhydro-(R)-3,5-O-benzylidene-L-rhamnonate (322726-61-4)

Guidance literature:

With potassium carbonate; In acetonitrile; at -78 - -10 ℃; for 0.666667h;

DOI:10.1016/j.tetasy.2004.07.032

Reference yield: 54.0%

methanol (67-56-1) + (R)-3,5-O-benzylidene-6-deoxy-2-O-trifluoromethanesulfonyl-L-glucono-1,4-lactone (322726-65-8) → methyl 2,4-anhydro-(R)-3,5-O-benzylidene-L-rhamnonate (322726-61-4) + methyl 2,4-anhydro (S)-3,5-O-benzylidene-L-rhamnonate

Guidance literature:

With potassium carbonate; at -78 ℃; for 1.3h;

DOI:10.1016/S0957-4166(00)00360-8

Reference yield:

L-rhamnose (73-34-7) → methyl 2,4-anhydro-(R)-3,5-O-benzylidene-L-rhamnonate (322726-61-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: barium carbonate; bromine / H₂O / 0 - 20 °C

1.2: 72 percent / hydrochloric acid / 48 h / 20 °C

2.1: 92 percent / pyridine / tetrahydrofuran / 1.83 h / -78 - 0 °C

3.1: 89 percent / potassium cabronate / acetonitrile / 0.67 h / -78 - -10 °C

With pyridine; bromine; potassium carbonate; barium carbonate; In tetrahydrofuran; water; acetonitrile;

DOI:10.1016/j.tetasy.2004.07.032

upstream raw materials:

methanol

(R)-3,5-O-benzylidene-6-deoxy-2-O-trifluoromethanesulfonyl-L-glucono-1,4-lactone

(R)-3,5-O-benzylidene-2-O-trifluoromethanesulfonyl-L-rhamnono-1,4-lactone

benzaldehyde dimethyl acetal

Downstream raw materials:

methyl 2,4-anhydro-5-O-benzyl-L-rhamnonate

methyl 2,4-anhydro-3-O-benzoyl-5-bromo-5,6-dideoxy-D-gulonate

methyl 2,4-anhydro-6-deoxy-5-O-benzyl-L-altronate

methyl 2,4-anhydro-3-azido-3,6-dideoxy-5-O-benzyl-L-altronate