octyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)-4,6-di-O-benzyl-3-C-methyl-β-D-galactopyranoside

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Chemical Name:octyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)-4,6-di-O-benzyl-3-C-methyl-β-D-galactopyranoside
CAS No.:259544-09-7
Molecular Formula:C₅₆H₇₀O₁₀
Molecular Weight:903.166
Hs Code.:

Synonyms:octyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)-4,6-di-O-benzyl-3-C-methyl-β-D-galactopyranoside

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Chemical Property of octyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)-4,6-di-O-benzyl-3-C-methyl-β-D-galactopyranoside

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Technology Process of octyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)-4,6-di-O-benzyl-3-C-methyl-β-D-galactopyranoside

There total 2 articles about octyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)-4,6-di-O-benzyl-3-C-methyl-β-D-galactopyranoside 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: 55.0%

: 917-54-4
methyllithium

: 259544-08-6
octyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)-4,6-di-O-benzyl-β-D-xylo-hexopyranosid-3-ulose

: 259544-09-7
octyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)-4,6-di-O-benzyl-3-C-methyl-β-D-galactopyranoside

Guidance literature:: In tetrahydrofuran; diethyl ether; at -78 - 40 ℃; for 1.5h;
DOI:10.1021/ja993004g

Reference yield:

: 155301-04-5
octyl 4,6-di-O-benzyl-2-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-gulopyranoside

: 259544-09-7
octyl 2,3,4-tri-O-benzyl-α-L-fucopyranosyl-(1->2)-4,6-di-O-benzyl-3-C-methyl-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: TiCl₄ / CH₂Cl₂ / 0.17 h / 4 °C

1.2: diisopropylethylamine / CH₂Cl₂ / 1 h / 4 °C

1.3: 85 percent / CH₂Cl₂ / 6 h / 0 - 4 °C

2.1: 90 percent / aq. H₂O₂; LiOH / tetrahydrofuran / 48 h / 4 °C

3.1: 98 percent / 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium*BF₄; diisopropylethylamine / acetonitrile / 2 h / 0 - 4 °C

4.1: H₂; 10 percent Pd(OH)2/C / methanol / 48 h / 20 °C / 760 Torr

5.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

6.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran; hexane / 0.5 h / -76.5 °C

6.2: dimethylaluminum chloride / tetrahydrofuran; hexane / 0.67 h / -76.5 °C

6.3: tetrahydrofuran; hexane / 1.08 h / -81.5 - -20 °C

With palladium dihydroxide; lithium hydroxide; hydrogen; dihydrogen peroxide; titanium tetrachloride; Dess-Martin periodane; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile; 1.1: complexation / 1.2: enolization / 1.3: benzyloxymethylation / 2.1: Hydrolysis / 3.1: Condensation / 4.1: Hydrogenation / 5.1: Oxidation / 6.1: Metallation / 6.2: Substitution / 6.3: Condensation;
DOI:10.1021/ja991175f