3-(6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-1-hydroxy-1-(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galactopyranosid-6-yl)propyne

Base Information

• Chemical Name: 3-(6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-1-hydroxy-1-(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galactopyranosid-6-yl)propyne
• CAS No.: 103814-09-1
• Molecular Formula: C₅₀H₅₈O₁₂
• Molecular Weight: 851.003

Synonyms:

Chemical Property of 3-(6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-1-hydroxy-1-(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galactopyranosid-6-yl)propyne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 3-(6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-1-hydroxy-1-(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galactopyranosid-6-yl)propyne

There total 12 articles about 3-(6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-yl)-1-hydroxy-1-(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galactopyranosid-6-yl)propyne 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:

methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galacto-heptodialdo-1,5-pyranoside (103882-24-2) + 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-oct-7-ynopyranose (103814-06-8) → 1(R)-1-(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galacto-hexapyranosid-6-yl)-3-(6-O-benzyl-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexapyranos-6-yl)-1-hydroxypropyne (103814-09-1,103882-25-3) + 1(S)-1-(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galacto-hexapyranosid-6-yl)-3-(6-O-benzyl-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexapyranos-6-yl)-1-hydroxypropyne (103814-09-1,103882-25-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1016/S0008-6215(00)90668-2

Reference yield:

methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galacto-heptodialdo-1,5-pyranoside (103882-24-2) + 6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-oct-7-ynopyranose (103814-06-8) → 1(R)-1-(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galacto-hexapyranosid-6-yl)-3-(6-O-benzyl-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexapyranos-6-yl)-1-hydroxypropyne (103814-09-1,103882-25-3) + 1(S)-1-(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galacto-hexapyranosid-6-yl)-3-(6-O-benzyl-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexapyranos-6-yl)-1-hydroxypropyne (103814-09-1,103882-25-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1016/S0008-6215(00)90668-2

Reference yield:

methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside (40653-32-5,641635-63-4) → 1(S)-1-(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galacto-hexapyranosid-6-yl)-3-(6-O-benzyl-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexapyranos-6-yl)-1-hydroxypropyne (103814-09-1,103882-25-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) DMSO-oxalyl chloride, 2.) LDA / 1.) THF, 2.) THF, -78 deg C, 1 h, room temp., 1 h

2: 1.52 g / pyridinium p-toluenesulfonate / dioxane; H₂O / 3 h / Heating

3: 106 mg / LDA / tetrahydrofuran / 0.25 h / 0 °C

With oxalyl dichloride; pyridinium p-toluenesulfonate; dimethyl sulfoxide; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1016/S0008-6215(00)90668-2

upstream raw materials:

methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galacto-heptodialdo-1,5-pyranoside

6-O-benzyl-7,8-dideoxy-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-oct-7-ynopyranose

methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside

7,8-dideoxy-1,2:3,4-di-O-isopropylidene-6(R)-hydroxy-α-D-galacto-oct-7-inopyranose

Downstream raw materials:

1(R)-O-benzyl-1-(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galacto-hexapyranosid-6-yl)-3-(6-O-benzyl-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexapyranos-6-yl)-2(R),3(R)-glycerol

1(R)-O-benzyl-1-(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galacto-hexapyranosid-6-yl)-3-(6-O-benzyl-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexapyranos-6-yl)-2(S),3(S)-glycerol

1(R)-O-benzyl-1-(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galacto-hexapyranosid-6-yl)-3-(6-O-benzyl-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexapyranos-6-yl)-prop-2-(Z)-ene

1(R)-1-(methyl 2,3,4-tri-O-benzyl-6-deoxy-β-D-galacto-hexapyranosid-6-yl)-3-(6-O-benzyl-1,2:3,4-di-O-isopropylidene-D-glycero-α-D-galacto-hexapyranos-6-yl)-1-hydroxypropyne

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