2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSYL FLUORIDE

Base Information

• Chemical Name: 2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSYL FLUORIDE
• CAS No.: 127061-08-9
• Molecular Formula: C27H29 F O4
• Molecular Weight: 436.523
• Mol file: 127061-08-9.mol

Synonyms:2,3,4-Tri-O-benzyl-L-fucopyranosylfluoride

Chemical Property of 2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSYL FLUORIDE

Chemical Property:

• Boiling Point: 533.8±50.0 °C(Predicted)
• PSA: 36.92000
• Density: 1.18±0.1 g/cm3(Predicted)
• LogP: 5.45690

Purity/Quality:

97% ^*data from raw suppliers

2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSYL FLUORIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSYL FLUORIDE

There total 2 articles about 2,3,4-TRI-O-BENZYL-L-FUCOPYRANOSYL FLUORIDE 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: 99.0%

ethyl 2,3,4-tri-O-benzyl-1-thio-α/β-L-fucopyranoside (169532-17-6,116391-11-8) → 2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride (127061-08-9)

Guidance literature:

With N-Bromosuccinimide; diethylamino-sulfur trifluoride; In dichloromethane;

DOI:10.1016/j.carres.2013.11.012

Reference yield: 85.0%

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol (162118-38-9) → 2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride (127061-08-9)

Guidance literature:

With 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1021/jo00115a027

Reference yield: 96.0%

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + 2,3,4-tri-O-benzyl-L-fucopyranosyl fluoride (127061-08-9) → (2',3',4'-tri-O-benzyl-β-L-fucopyranosyl)-(1→6)-methyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Guidance literature:

With 4 A molecular sieve; lithium perchlorate; In dichloromethane; at 25 ℃; for 24h;

DOI:10.1016/0040-4039(95)00637-R

upstream raw materials:

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

ethyl 2,3,4-tri-O-benzyl-1-thio-α/β-L-fucopyranoside

Downstream raw materials:

(2R,3S,4R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-((3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,4-dihydro-2H-pyran-3-ol

C₆₈H₇₇NO₁₈

(-)-O-<2,3,4-tri-O-benzyl-α-L-fucopyranosyl>-(1<*>3)-1,5-anhydro-4-O-acetyl-2-deoxy-5(S)-phenyl-L-xylo-pent-1-enopyranose

O-<2,3,4-tri-O-benzyl-β-L-fucopyranosyl>-(1<*>3)-1,5-anhydro-4-O-acetyl-2-deoxy-5(S)-phenyl-L-xylo-pent-1-enopyranose

Refernces

• 1、 Huang,Wong. "Synthesis of biologically active sialyl Lewis X mimetics". . p. 3100 - 3106. Retrieved 2007/10/02.