(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

Base Information

• Chemical Name: (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
• CAS No.: 904300-37-4
• Molecular Formula: C₄₉H₅₆O₉S
• Molecular Weight: 821.044
• Mol file: 904300-37-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 1 articles about (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 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: 47.0%

2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl bromide (67773-43-7) + Ethyl 4-O-benzyl-1-thio-α-D-rhamnopyranoside (151669-31-7) → (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)

Guidance literature:

With 4 A molecular sieve; tetraethylammonium bromide; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 40h;

DOI:10.1016/j.carres.2006.03.015

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:

(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) → 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 (904300-39-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / pyridine / 24 h / 20 °C

2: 67 percent / 4 Angstroem molecular sieves; N-iodosuccinimide; silver trifluoromethanesulfonate / CH₂Cl₂ / 2.5 h

With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; In pyridine; dichloromethane;

DOI:10.1016/j.carres.2006.03.015

upstream raw materials:

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

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

Downstream raw materials:

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

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