(2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol

Base Information

• Chemical Name: (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol
• CAS No.: 59531-24-7
• Molecular Formula: C₃₄H₃₆O₆
• Molecular Weight: 540.656
• Mol file: 59531-24-7.mol

Synonyms:2,3,4,6-tetra-O-benzyl-D-glucopyranoside

Chemical Property of (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol

Chemical Property:

• Boiling Point: 672.4±55.0 °C(Predicted)
• PKA: 11.87±0.70(Predicted)
• Density: 1.22±0.1 g/cm3(Predicted)

Purity/Quality:

90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol

There total 342 articles about (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)Methyl)tetrahydro-2H-pyran-2-ol 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: 100.0%

1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside (74666-83-4,105990-37-2,125354-46-3,125354-47-4,125411-99-6,108739-67-9) → 2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; water; at 20 ℃; for 1h;

DOI:10.1002/chem.200600262

Reference yield: 100.0%

2,3,4,6-tetra-O-benzyl-1-O-propynyl-D-glucopyranoside → 2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9)

Guidance literature:

With water; gold(III) chloride; In acetonitrile; at 20 ℃; for 12h;

DOI:10.1021/ja062425c

Reference yield: 100.0%

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside (38184-10-0) → 2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; water; at 20 ℃; for 1h;

DOI:10.1002/chem.200600262

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-N,N-dimethyl-D-gluconamid

methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside

2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

(2R,3R,4S,5R)-1,3,4,5-tetrakis(benzyloxy)-6,6-bis(ethylthio)hexan-2-ol

2,3:4,5-di-O-isopropylidene-1-O-<2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl>-β-D-fructopyranose

2,3:4,5-di-O-isopropylidene-1-O-<2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl>-β-D-fructopyranose

2-((3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrimidine