3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene

Base Information

• Chemical Name: 3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene
• CAS No.: 82659-55-0
• Molecular Formula: C₃₇H₄₀O₅
• Molecular Weight: 564.722
• Mol file: 82659-55-0.mol

Synonyms:3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene

Chemical Property of 3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene

There total 13 articles about 3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene 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: 95.0%

benzyl bromide (100-39-0) + 2,6-anhydro-7,8,9-trideoxy-D-glycero-L-galacto-non-8-enitol (133697-14-0) → 3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene (82659-55-0)

Guidance literature:

2,6-anhydro-7,8,9-trideoxy-D-glycero-L-galacto-non-8-enitol; With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 2h;

benzyl bromide; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1135/cccc20051411

Reference yield: 95.0%

2,3,4,6-tetra-O-benzyl-D-galactopyranosyl isoquinoline-1-carboxylate + allyl-trimethyl-silane (762-72-1) → 3-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)prop-1-ene (82659-57-2) + 3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene (82659-55-0)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at 20 ℃; Solvent; stereoselective reaction; Molecular sieve; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.0c01041

Reference yield: 83.0%

2,3,4,6-tetrakis-O-(phenylmethyl)-1-O-acetyl-α-D-galactopyranose (3866-62-4,3964-13-4,56822-48-1,56822-49-2,78136-22-8,80300-30-7,80300-97-6,83462-68-4,83462-69-5,94943-10-9) + allyl-trimethyl-silane (762-72-1) → 3-(2',3',4',6'-tetra-O-benzyl-α-D-galactopyranosyl)prop-1-ene (82659-55-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃; for 0.333333h; Inert atmosphere; Sonication;

DOI:10.1016/j.tetlet.2010.10.113

upstream raw materials:

(4-Nitro-phenyl)-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-methanone

allyl-trimethyl-silane

2,3,4,6-tetra-O-benzyl-D-galactonolactone

allylmagnesium bromide

Downstream raw materials:

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

3-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)propanol

2-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)ethyl aldehyde

(3aR,5R,6S,7S,7aS)-6,7-Bis-benzyloxy-5-benzyloxymethyl-2-iodomethyl-hexahydro-furo[3,2-b]pyran