(3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran

Base Information

• Chemical Name: (3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran
• CAS No.: 67576-77-6
• Molecular Formula: C28H32O5
• Molecular Weight: 448.559
• Hs Code.: 29400000
• DSSTox Substance ID: DTXSID10370145
• Mol file: 67576-77-6.mol

Synonyms:67576-77-6;(3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran;Methyl 2,3,4-tri-O-benzyl-L-fucopyranoside;(3S,4R,5R,6S)-2-methoxy-6-methyl-3,4,5-tris(phenylmethoxy)oxane;METHYL-2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSE;ST50405945;DTXSID10370145;W-203498

Chemical Property of (3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran

Chemical Property:

• Vapor Pressure: 9.75E-12mmHg at 25°C
• Refractive Index: 1.5400 (estimate)
• Boiling Point: 553.7°Cat760mmHg
• Flash Point: 215.4°C
• PSA: 46.15000
• Density: 1.15g/cm³
• LogP: 5.13380
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 448.22497412
• Heavy Atom Count: 33
• Complexity: 524

Purity/Quality:

98%Min ^*data from raw suppliers

Methyl 2,3,4-tri-O-benzyl-L-fucopyranoside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Isomeric SMILES: C[C@H]1[C@H]([C@H]([C@@H](C(O1)OC)OCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4

Technology Process of (3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-2-methoxy-6-methyltetrahydro-2H-pyran

There total 10 articles about (3S,4R,5R,6S)-3,4,5-Tris(benzyloxy)-2-methoxy-6-methyltetrahydro-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: 96.7%

methyl 2,3,4-tri-O-benzyl-6-O-tosyl-α-D-mannopyranoside (65518-53-8) → methyl 2,3,4-tri-O-benzyl-α-D-rhamnopyranoside (33639-74-6,59055-57-1,67576-77-6,73174-44-4,73174-45-5,74841-88-6,83916-89-6,99212-28-9,73174-55-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; benzene; for 0.5h; Heating;

Reference yield: 63.0%

methanol (67-56-1) + 6-deoxy-L-galactose (73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6) + benzyl bromide (100-39-0) → 1-O-methyl 2,3,4-tri-O-benzyl-L-fucopyranoside (67576-77-6)

Guidance literature:

methanol; 6-deoxy-L-galactose; at 65 ℃; for 36h;

benzyl bromide; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1371/journal.pone.0112822

Reference yield:

methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-α-D-manno-pyranoside (291753-79-2) → methyl 2,3,4-tri-O-benzyl-α-D-rhamnopyranoside (33639-74-6,59055-57-1,67576-77-6,73174-44-4,73174-45-5,74841-88-6,83916-89-6,99212-28-9,73174-55-7)

Guidance literature:

methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-α-D-manno-pyranoside; With sodium tetrahydroborate; In dimethyl sulfoxide; at 100 ℃;

In dimethyl sulfoxide; acetone; for 1h; Reflux;

DOI:10.1039/c2cc17623h

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-6-O-tosyl-α-D-mannopyranoside

methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside

methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside

methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-α-D-manno-pyranoside

Downstream raw materials:

(2S,3S,4S,5S,6R)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol

1-O-(4-pentenyl) 2,3,4-tri-O-benzyl-α-L-fucopyranoside

2,3,4-tri-O-benzyl-α-L-fucopyranosyl chloride

2,3,4-tri-O-benzyl-6-deoxy-α-D-mannopyranosyl (n-phenyl)trifluoroacetimidate

Refernces

• 1、 Nakagawa, Yu,Doi, Takashi,Taketani, Takara,Takegoshi,Igarashi, Yasuhiro,Ito, Yukishige. "Mannose-binding geometry of pradimicin A". supporting information. p. 10516 - 10525. Retrieved 2013/08/23.
• 2、 Kondo, Hirosato,Aoki, Shin,Ichikawa, Yoshitaka,Halcomb, Randall L.,Ritzen, Helena,Wong, Chi-Huey. "Glycosyl Phosphites as Glycosylation Reagents: Scope and Mechanism". . p. 864 - 877. Retrieved 2007/10/02.