ethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-D-rhamnopyranoside

Base Information

• Chemical Name: ethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-D-rhamnopyranoside
• CAS No.: 904300-38-5
• Molecular Formula: C₅₆H₆₀O₁₀S
• Molecular Weight: 925.152

Synonyms:ethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-D-rhamnopyranoside

Chemical Property of ethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-D-rhamnopyranoside

Chemical Property:

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Technology Process of ethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-D-rhamnopyranoside

There total 3 articles about ethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-D-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: 85.0%

(2R,3S,4R,5R,6R)-5-Benzyloxy-2-ethylsulfanyl-6-methyl-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol (904300-37-4) + benzoyl chloride (98-88-4) → ethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-D-rhamnopyranoside (904300-38-5)

Guidance literature:

In pyridine; at 20 ℃; for 24h;

DOI:10.1016/j.carres.2006.03.015

Reference yield:

2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl bromide (67773-43-7) → ethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-D-rhamnopyranoside (904300-38-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 47 percent / Et₄NBr; 4 Angstroem molecular sieves / CH₂Cl₂; dimethylformamide / 40 h / 20 °C

2: 85 percent / pyridine / 24 h / 20 °C

With 4 A molecular sieve; tetraethylammonium bromide; In pyridine; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2006.03.015

Reference yield:

Ethyl 4-O-benzyl-1-thio-α-D-rhamnopyranoside (151669-31-7) → ethyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-D-rhamnopyranoside (904300-38-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 47 percent / Et₄NBr; 4 Angstroem molecular sieves / CH₂Cl₂; dimethylformamide / 40 h / 20 °C

2: 85 percent / pyridine / 24 h / 20 °C

With 4 A molecular sieve; tetraethylammonium bromide; In pyridine; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2006.03.015

upstream raw materials:

(2R,3S,4R,5R,6R)-5-Benzyloxy-2-ethylsulfanyl-6-methyl-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol

benzoyl chloride

2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl bromide

Ethyl 4-O-benzyl-1-thio-α-D-rhamnopyranoside

Downstream raw materials:

methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-D-rhamnopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

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