(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

Base Information

• Chemical Name: (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
• CAS No.: 438216-18-3
• Molecular Formula: C₇₀H₈₀O₁₆
• Molecular Weight: 1177.4
• Mol file: 438216-18-3.mol

Synonyms:(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

Chemical Property of (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

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-O-(1->3)-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-O-(1->4)]-6-O-benzyl-1,2-dideoxy-D-glucopyranose

There total 7 articles about (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 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: 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:

1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside (135214-83-4) → (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:

Multi-step reaction with 5 steps

1.1: 97 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / 20 °C

2.1: 92 percent / NaBH₃CN; HCl; 4 Angstroem molecular sieves / diethyl ether; tetrahydrofuran / 20 °C

3.1: 1,1,3,3-tetramethylurea; 4 Angsroem molecular sieves / CH₂Cl₂ / 20 °C

3.2: AgOTf / CH₂Cl₂ / 24 h / 20 °C

4.1: 85 percent / NaOMe / methanol / 2 h / 45 °C

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

5.2: 48 percent / AgOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 0 - 20 °C

With hydrogenchloride; dmap; 4 A molecular sieve; sodium methylate; sodium hydride; sodium cyanoborohydride; triethylamine; tetramethylurea; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo0110956

Reference yield:

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol (162118-38-9) → (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:

Multi-step reaction with 4 steps

1.1: 89 percent / Et₃N / CH₂Cl₂ / 24 h / 20 °C

2.1: 1,1,3,3-tetramethylurea; 4 Angsroem molecular sieves / CH₂Cl₂ / 20 °C

2.2: AgOTf / CH₂Cl₂ / 24 h / 20 °C

3.1: 85 percent / NaOMe / methanol / 2 h / 45 °C

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

4.2: 48 percent / AgOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 0 - 20 °C

With 4 A molecular sieve; sodium methylate; sodium hydride; triethylamine; tetramethylurea; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo0110956

upstream raw materials:

(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-(methoxycarbonyl)-2-cyclohexylethyloxy]-β-D-galactopyranosyl 2-thiopyridyl carbonate

1,5-Anhydro-2-deoxy-4,6-O-(phenylmethylene)-D-arabino-hexopyranoside

(3S,4R,5R,6S)-3,4,5-tris(benzyloxy)-6-methyltetrahydro-2H-pyran-2-ol

Downstream raw materials:

(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

(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