2,3,4-tri-O-benzyl-α-D-xylopyranosyl fluoride

Base Information

• Chemical Name: 2,3,4-tri-O-benzyl-α-D-xylopyranosyl fluoride
• CAS No.: 95898-05-8
• Molecular Formula: C₂₆H₂₇FO₄
• Molecular Weight: 422.496
• Mol file: 95898-05-8.mol

Synonyms:2,3,4-tri-O-benzyl-α-D-xylopyranosyl fluoride

Chemical Property of 2,3,4-tri-O-benzyl-α-D-xylopyranosyl fluoride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4-tri-O-benzyl-α-D-xylopyranosyl fluoride

There total 9 articles about 2,3,4-tri-O-benzyl-α-D-xylopyranosyl 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: 100.0%

1-O-acetyl 2,3,4-tri-O-benzyl-α,β-D-xylopyranose (95898-04-7) → 2,3,4-tri-O-benzyl-α-D-xylopyranosyl fluoride (95898-05-8)

Guidance literature:

With hydrogen fluoride; In dichloromethane; at -70 ℃; for 0.5h;

DOI:10.1002/hlca.19850680134

Reference yield:

2,3,4-tri-O-benzyl-D-xylopyranose (18039-26-4,20787-16-0,20787-21-7,77943-32-9,77943-33-0,89615-43-0,89615-44-1,90899-55-1) → 2,3,4-tri-O-benzyl-α-D-xylopyranosyl fluoride (95898-05-8) + 2,3,4-tri-O-benzyl-β-D-xylopyranosyl fluoride

Guidance literature:

With bis(p-methoxyphenyl)methanone; N-ethyl-N,N-diisopropylamine; sulfur(VI) hexafluoride; In 1,2-dichloro-ethane; at 20 ℃; for 20h; under 760.051 Torr; Overall yield = 80 percent; Overall yield = 33.7 mg; Sealed tube; Irradiation;

DOI:10.1021/acs.orglett.0c03915

Reference yield:

benzyl bromide (100-39-0) → 2,3,4-tri-O-benzyl-α-D-xylopyranosyl fluoride (95898-05-8) + 2,3,4-tri-O-benzyl-β-D-xylopyranosyl fluoride

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydride; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2: water; N-Bromosuccinimide / acetone / 0 - 20 °C

3: N-ethyl-N,N-diisopropylamine; sulfur(VI) hexafluoride; bis(p-methoxyphenyl)methanone / 1,2-dichloro-ethane / 20 h / 20 °C / 760.05 Torr / Sealed tube; Irradiation

With N-Bromosuccinimide; bis(p-methoxyphenyl)methanone; water; tetra-(n-butyl)ammonium iodide; sodium hydride; N-ethyl-N,N-diisopropylamine; sulfur(VI) hexafluoride; In 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acs.orglett.0c03915

upstream raw materials:

1-O-acetyl 2,3,4-tri-O-benzyl-α,β-D-xylopyranose

2,3,4-tri-O-benzyl-D-xylopyranose

benzyl bromide

D-Xylose

Downstream raw materials:

(2S,3R,4S,5R)-2-{(2S,3R,4S,5S,6R)-2-[(2S,4aS,8aR)-5-(2-Furan-3-yl-ethyl)-1,1,4a,6-tetramethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-2-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy}-tetrahydro-pyran-3,4,5-triol

(2R,3R,4S,5R)-2-{(2R,3R,4S,5S,6R)-2-[(2R,4aR,8aS)-5-(2-Furan-3-yl-ethyl)-1,1,4a,6-tetramethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-2-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy}-tetrahydro-pyran-3,4,5-triol

(2S,3R,4S,5R)-2-{(2S,3R,4S,5S,6R)-2-[(2R,4aR,8aS)-5-(2-Furan-3-yl-ethyl)-1,1,4a,6-tetramethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-2-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy}-tetrahydro-pyran-3,4,5-triol

baiyunoside

Refernces

• 1、 Kunz, Horst,Sager, Wilfried. "Stereoselective Glycosylation of Alcohols and Silyl Ethers Using Glycosyl Fluorides and Boron Trifluoride Etherate". . p. 283 - 287. Retrieved 2007/10/02.