methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-lyxo-hept-2-ulopyranosid)onate

Base Information

• Chemical Name: methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-lyxo-hept-2-ulopyranosid)onate
• CAS No.: 211935-00-1
• Molecular Formula: C₃₀H₃₄O₇
• Molecular Weight: 506.596
• Mol file: 211935-00-1.mol

Synonyms:methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-lyxo-hept-2-ulopyranosid)onate

Chemical Property of methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-lyxo-hept-2-ulopyranosid)onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-lyxo-hept-2-ulopyranosid)onate

There total 4 articles about methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-lyxo-hept-2-ulopyranosid)onate 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: 87.0%

methanol (67-56-1) + 2,6-anhydro-4,5,7-tri-O-benzyl-1-(propane-1,3-diyl-dithioacetal)-1,3-dideoxy-D-lyxo-hept-1-enitol (211934-98-4) → methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-lyxo-hept-2-ulopyranosid)onate (211935-00-1)

Guidance literature:

With N-Bromosuccinimide; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4020(99)00049-6

Reference yield:

(2R,3R,4R)-3,4-bis-benzyloxy-2-benzyloxymethyltetrahydropyran-5-one (72605-77-7,79999-46-5) → methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-lyxo-hept-2-ulopyranosid)onate (211935-00-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) KHMDS / 1.) THF, toluene, -78 deg C, 1 h, 2.) THF, -78 deg C -> 0 deg C, 3 h

2: 87 percent / NBS / CH₂Cl₂ / 0.5 h / Ambient temperature

With N-Bromosuccinimide; potassium hexamethylsilazane; In dichloromethane;

DOI:10.1016/S0040-4020(99)00049-6

Reference yield:

2,6-anhydro-4,5,7-tri-O-benzyl-1-(propane-1,3-diyl-dithioacetal)-1,3-dideoxy-D-lyxo-hept-1-enitol (211934-98-4) → methyl (methyl 4,5,7-tri-O-benzyl-3-deoxy-α-D-lyxo-hept-2-ulopyranosid)onate (211935-00-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / TMSOTf / CH₂Cl₂ / 2 h / -20 - 20 °C

2: NBS; H₂O / tetrahydrofuran / 0.5 h

3: methanol; diethyl ether

With N-Bromosuccinimide; trimethylsilyl trifluoromethanesulfonate; water; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1: Addition / 2: oxidative hydrolysis / 3: Esterification;

upstream raw materials:

methanol

2,6-anhydro-4,5,7-tri-O-benzyl-1-(propane-1,3-diyl-dithioacetal)-1,3-dideoxy-D-lyxo-hept-1-enitol

diazomethane

(2R,3R,4R)-3,4-bis-benzyloxy-2-benzyloxymethyltetrahydropyran-5-one

Downstream raw materials:

(2R,4R,5R,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-2-carboxylic acid methyl ester