ethyl 2-O-benzoyl-4-O-benzyl-3-O-levulinoyl-1-thio-α-L-rhamnopyranoside

Base Information

• Chemical Name: ethyl 2-O-benzoyl-4-O-benzyl-3-O-levulinoyl-1-thio-α-L-rhamnopyranoside
• CAS No.: 927680-44-2
• Molecular Formula: C₂₇H₃₂O₇S
• Molecular Weight: 500.613
• Mol file: 927680-44-2.mol

Synonyms:ethyl 2-O-benzoyl-4-O-benzyl-3-O-levulinoyl-1-thio-α-L-rhamnopyranoside

Chemical Property of ethyl 2-O-benzoyl-4-O-benzyl-3-O-levulinoyl-1-thio-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-O-benzoyl-4-O-benzyl-3-O-levulinoyl-1-thio-α-L-rhamnopyranoside

There total 1 articles about ethyl 2-O-benzoyl-4-O-benzyl-3-O-levulinoyl-1-thio-α-L-rhamnopyranoside 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: 86.0%

levulinic acid (123-76-2) + ethyl 2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside (142776-67-8) → ethyl 2-O-benzoyl-4-O-benzyl-3-O-levulinoyl-1-thio-α-L-rhamnopyranoside (927680-44-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/chem.200601245

Reference yield: 78.0%

ethyl 2-O-benzoyl-4-O-benzyl-3-O-levulinoyl-1-thio-α-L-rhamnopyranoside (927680-44-2) + 3-[(N-benzyloxycarbonyl)amino]propyl-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside (927680-45-3) → 3-[(N-benzyloxycarbonyl)amino]propyl-O-(2-O-benzoyl-4-O-benzyl-3-O-levulinoyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside (927680-46-4)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; In dichloromethane; at 0 ℃;

DOI:10.1002/chem.200601245

Reference yield:

ethyl 2-O-benzoyl-4-O-benzyl-3-O-levulinoyl-1-thio-α-L-rhamnopyranoside (927680-44-2) → C65H74N2O16

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; trifluoromethaneulfonic acid / CH₂Cl₂ / 0 °C

2: 93 percent / hyrazine acetate / methanol; CH₂Cl₂ / 4 h / 20 °C

3: 76 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; trifluoromethaneulfonic acid / CH₂Cl₂ / 0 °C

4: 93 percent / hyrazine acetate / methanol; CH₂Cl₂ / 4 h / 20 °C

5: 51 percent / silver(I) oxide / dimethyl sulfide / tetrahydrofuran / 20 °C

6: 99 percent / 1,3-propanedithiol; triethylamine; pyridine / H₂O / 20 °C

With pyridine; 1.3-propanedithiol; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrazinium monoacetate; triethylamine; silver(l) oxide; dimethylsulfide; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1002/chem.200601245

upstream raw materials:

levulinic acid

ethyl 2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

3-[(N-benzyloxycarbonyl)amino]propyl-O-(2-O-benzoyl-4-O-benzyl-3-O-levulinoyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

3-[(N-benzyloxycarbonyl)amino]propyl-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-azido-3-O-benzyl-4,6-dideoxy-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

3-[(N-benzyloxycarbonyl)amino]propyl-O-(4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl)-(1->3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside