(2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran

Base Information

• Chemical Name: (2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran
• CAS No.: 1380505-22-5
• Molecular Formula: C₄₄H₅₄O₆
• Molecular Weight: 678.909
• Mol file: 1380505-22-5.mol

Synonyms:(2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran

Chemical Property of (2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran

There total 11 articles about (2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran 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%

(-)-menthol (2216-51-5) + 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetimidate (90358-01-3) → (2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran (1380505-22-5)

Guidance literature:

With phenyltrifluorosilane; In dichloromethane; at -40 ℃; for 1h; optical yield given as %de; diastereoselective reaction;

DOI:10.1002/adsc.201100933

Reference yield:

(-)-menthol (2216-51-5) + phenyl (2,3,4,6-tetra-O-benzyl)-1-thio-β-D-galactopyranoside S-oxide (117307-18-3) → (2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran (1380505-22-5) + (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran (343565-52-6)

Guidance literature:

With gold(III) chloride; silver trifluoromethanesulfonate; In dichloromethane; at 35 - 39 ℃; for 0.333333h; Overall yield = 68 %; Overall yield = 70 mg; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.carres.2016.11.012

Reference yield:

(-)-menthol (2216-51-5) + phenyl-2,3,4,6-tetra-O-benzyl-1-seleno-β-D-galactopyrannoside (139903-48-3,139903-49-4,143995-67-9) → (2R,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran (1380505-22-5) + (2R,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)oxy)tetrahydro-2H-pyran (343565-52-6)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; carbon tetrabromide; diphenyl diselenide; In dichloromethane; for 39h; Overall yield = 55 %; stereoselective reaction; Irradiation;

DOI:10.1016/j.carres.2013.01.004

upstream raw materials:

(-)-menthol

2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl trichloroacetimidate

phenyl-2,3,4,6-tetra-O-benzyl-1-seleno-β-D-galactopyrannoside

phenyl-2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside