2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl 2-thiopyridyl carbonate

Base Information

• Chemical Name: 2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl 2-thiopyridyl carbonate
• CAS No.: 438216-13-8
• Molecular Formula: C₃₆H₃₉NO₁₀S
• Molecular Weight: 677.772
• Mol file: 438216-13-8.mol

Synonyms:2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl 2-thiopyridyl carbonate

Chemical Property of 2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl 2-thiopyridyl carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl 2-thiopyridyl carbonate

There total 1 articles about 2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl 2-thiopyridyl carbonate 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: 80.0%

Di-S-(2-pyridyl) dithiocarbonate (55277-90-2) + 2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-D-galactopyranose → 2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl 2-thiopyridyl carbonate (438216-13-8)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jo0110956

Reference yield: 48.0%

(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)-6-O-benzyl-1,2,-dideoxy-D-glucopyranose (438216-17-2) + 2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl 2-thiopyridyl carbonate (438216-13-8) → (2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl-O-(1->3)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)]-6-O-benzyl-1,2-dideoxy-D-glucopyranose (438216-18-3)

Guidance literature:

(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)-6-O-benzyl-1,2,-dideoxy-D-glucopyranose; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.5h;

2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl 2-thiopyridyl carbonate; With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; Further stages.;

DOI:10.1021/jo0110956

Reference yield:

2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl 2-thiopyridyl carbonate (438216-13-8) → (3-O-[(S)-1-(oxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl-O-(1->3)-[α-L-fucopyranosyl)-O-(1->4)]-1,2-dideoxy-D-glucopyranose

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 48 percent / AgOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 0 - 20 °C

2.1: aq. LiOH / tetrahydrofuran / 48 h / 20 °C

3.1: 90 percent / NaOme / methanol / 2 h / Heating

4.1: H₂; AcOH / Pd(OH)2/C / dioxane / 40 h / 20 °C

With lithium hydroxide; hydrogen; sodium methylate; sodium hydride; acetic acid; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol;

DOI:10.1021/jo0110956

upstream raw materials:

Di-S-(2-pyridyl) dithiocarbonate

Downstream raw materials:

(2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl-O-(1->3)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)]-6-O-benzyl-1,2-dideoxy-D-glucopyranose

(4,6-O-benzylidene-3-O-[(S)-1-(oxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl-O-(1->3)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)]-6-O-benzyl-1,2-dideoxy-D-glucopyranose

(2-O-benzoyl-4,6-O-benzylidene-3-O-[(S)-1-(oxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl-O-(1->3)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)]-6-O-benzyl-1,2-dideoxy-D-glucopyranose