(2R,3R,4R)-3,4-bis(benzyloxy)-2-(2S,3R,4S,5S,6R)-(((3,4,5-tris-(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4-dihydro-2H-pyran

Base Information

• Chemical Name: (2R,3R,4R)-3,4-bis(benzyloxy)-2-(2S,3R,4S,5S,6R)-(((3,4,5-tris-(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4-dihydro-2H-pyran
• CAS No.: 321734-92-3
• Molecular Formula: C₅₄H₅₆O₉
• Molecular Weight: 849.033
• Mol file: 321734-92-3.mol

Synonyms:(2R,3R,4R)-3,4-bis(benzyloxy)-2-(2S,3R,4S,5S,6R)-(((3,4,5-tris-(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4-dihydro-2H-pyran

Chemical Property of (2R,3R,4R)-3,4-bis(benzyloxy)-2-(2S,3R,4S,5S,6R)-(((3,4,5-tris-(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4-dihydro-2H-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R)-3,4-bis(benzyloxy)-2-(2S,3R,4S,5S,6R)-(((3,4,5-tris-(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4-dihydro-2H-pyran

There total 8 articles about (2R,3R,4R)-3,4-bis(benzyloxy)-2-(2S,3R,4S,5S,6R)-(((3,4,5-tris-(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4-dihydro-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: 80.0%

(2R,3R,4R)-(3,4-bis(benzyloxy)-3,4-dihydro-2H-pyran-2-yl)methanol (130323-37-4) + 2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-galactopyranosyl fluoride (101966-50-1) → 3,4-di-O-benzyl-6-O-(2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol + (2R,3R,4R)-3,4-bis(benzyloxy)-2-(2S,3R,4S,5S,6R)-(((3,4,5-tris-(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4-dihydro-2H-pyran (321734-92-3)

Guidance literature:

With silver perchlorate; tin(ll) chloride; 2,4-di-tert-butyl-6-methylpyridine; In diethyl ether; at 20 ℃; for 30h;

DOI:10.1016/S0957-4166(00)00366-9

Reference yield:

2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl iodide (53008-62-1,53008-61-0) + (2R,3R,4R)-(3,4-bis(benzyloxy)-3,4-dihydro-2H-pyran-2-yl)methanol (130323-37-4) → (2R,3R,4R)-3,4-bis(benzyloxy)-2-(2S,3R,4S,5S,6R)-(((3,4,5-tris-(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4-dihydro-2H-pyran (321734-92-3)

Guidance literature:

(2R,3R,4R)-(3,4-bis(benzyloxy)-3,4-dihydro-2H-pyran-2-yl)methanol; With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In benzene; at 65 ℃; for 0.166667h; Inert atmosphere; Molecular sieve;

2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl iodide; In benzene; at 65 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm400949h

Reference yield:

3,4,6-tri-O-benzyl-D-galactal (80040-79-5) → (2R,3R,4R)-3,4-bis(benzyloxy)-2-(2S,3R,4S,5S,6R)-(((3,4,5-tris-(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)-3,4-dihydro-2H-pyran (321734-92-3)

Guidance literature:

Multi-step reaction with 4 steps

1: dimethyldioxirane / CH₂Cl₂ / 0.5 h / 0 °C

2: TBAF / tetrahydrofuran / 30 h / 20 °C

3: 88 percent / NaH / dimethylformamide / 1 h / 0 - 20 °C

4: 80 percent / 6-methyl-2,4-di-tert-butylpyridine; silver perchlorate; SnCl₂ / diethyl ether / 30 h / 20 °C

With tetrabutyl ammonium fluoride; silver perchlorate; 3,3-dimethyldioxirane; sodium hydride; tin(ll) chloride; 2,4-di-tert-butyl-6-methylpyridine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1: Epoxidation / 2: Ring cleavage / 3: Alkylation / 4: glycosylation;

DOI:10.1016/S0957-4166(00)00366-9

upstream raw materials:

(2R,3R,4R)-(3,4-bis(benzyloxy)-3,4-dihydro-2H-pyran-2-yl)methanol

2,3,4,6-tetrakis-O-(phenylmethyl)-β-D-galactopyranosyl fluoride

3,4,6-tri-O-benzyl-D-galactal

1,2-anhydro-3,4,6-tri-O-benzyl-D-galactopyranose