(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-heptonate

Base Information

• Chemical Name: (methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-heptonate
• CAS No.: 137945-91-6
• Molecular Formula: C₄₆H₆₀O₁₃
• Molecular Weight: 820.975
• Mol file: 137945-91-6.mol

Synonyms:(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-heptonate

Chemical Property of (methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-heptonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-heptonate

There total 6 articles about (methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-heptonate 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: 65.0%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-heptonic acid (131444-71-8) → (methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-heptonate (137945-91-6)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1021/jo00041a017

Reference yield:

2,3,5,6-di-O-isopropylidene-D-mannofuranose (7757-38-2,14131-84-1,23262-78-4,27108-13-0,33823-04-0,34685-42-2,57819-52-0,78039-08-4,78039-12-0,78964-16-6,94842-76-9,149342-31-4) → (methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-heptonate (137945-91-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 71 percent / n-BuLi / tetrahydrofuran; hexane / 15 h / 20 °C

2: 98 percent / pyridine, DMAP / 32 h / Ambient temperature

3: 1) 9-BBN, 2) 25percent H₂O₂, NaOH / 1) THF, 0 deg C to rt, 2 h, 2) THF, H₂O, 0 deg C

4: RuCl₃*H₂O, NaIO₄ / CCl₄; acetonitrile; H₂O / 1 h / Ambient temperature

5: 65 percent / DCC, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

With pyridine; dmap; ruthenium trichloride; sodium hydroxide; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; dihydrogen peroxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; water; acetonitrile;

DOI:10.1021/jo00041a017

Reference yield:

pivaloyl chloride (3282-30-2) → (methyl 2,3,6-tri-O-benzyl-α-D-glucopyranosid-4-yl) 2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-heptonate (137945-91-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / pyridine, DMAP / 32 h / Ambient temperature

2: 1) 9-BBN, 2) 25percent H₂O₂, NaOH / 1) THF, 0 deg C to rt, 2 h, 2) THF, H₂O, 0 deg C

3: RuCl₃*H₂O, NaIO₄ / CCl₄; acetonitrile; H₂O / 1 h / Ambient temperature

4: 65 percent / DCC, DMAP / CH₂Cl₂ / 0.5 h / Ambient temperature

With pyridine; dmap; ruthenium trichloride; sodium hydroxide; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; dicyclohexyl-carbodiimide; In tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/jo00041a017

upstream raw materials:

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

2-deoxy-3,4:6,7-di-O-isopropylidene-5-O-pivaloyl-D-manno-heptonic acid

2,3,5,6-di-O-isopropylidene-D-mannofuranose

pivaloyl chloride