ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-1-thio-α-L-rhamnopyranoside

Base Information

Chemical Name:ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-1-thio-α-L-rhamnopyranoside
CAS No.:877606-75-2
Molecular Formula:C₃₇H₄₆O₁₀S
Molecular Weight:682.832
Hs Code.:

Synonyms:ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-1-thio-α-L-rhamnopyranoside

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Chemical Property of ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-1-thio-α-L-rhamnopyranoside

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Technology Process of ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-1-thio-α-L-rhamnopyranoside

There total 7 articles about ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-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: 85.0%

: 877606-74-1
ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-3,4-O-(2',3'-diethoxybutane-2',3'-diyl)-1-thio-α-L-rhamnopyranoside

: 877606-75-2
ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-1-thio-α-L-rhamnopyranoside

Guidance literature:: With trifluoroacetic acid; In water; at 20 ℃; for 0.5h;
DOI:10.1016/j.carres.2005.11.007

Reference yield:

: 877606-70-7
ethyl 3,4-O-(2',3'-diethoxybutane-2',3'-diyl)-1-thio-α-L-rhamnopyranoside

: 877606-75-2
ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 1 h / 0 °C

2: 83 percent / NaOMe / methanol; H₂O / 3 h / 20 °C / pH 9 - 10

3: DMSO / 20 °C

4: NaBH₄ / methanol; CH₂Cl₂ / 6 h / 20 °C

5: pyridine / 12 h / 20 °C

6: 85 percent / TFA / H₂O / 0.5 h / 20 °C

With sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; dimethyl sulfoxide; trifluoroacetic acid; In pyridine; methanol; dichloromethane; water; 2: Zemplen deacetylation;
DOI:10.1016/j.carres.2005.11.007

Reference yield:

: (2S,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2S,3S,4aS,5S,7S,8R,8aR)-2,3-diethoxy-7-ethylsulfanyl-2,3,5-trimethyl-hexahydro-pyrano[3,4-b][1,4]dioxin-8-yloxy)-tetrahydro-pyran-3-ol

: 877606-75-2
ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->2)-1-thio-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / 12 h / 20 °C

2: 85 percent / TFA / H₂O / 0.5 h / 20 °C

With trifluoroacetic acid; In pyridine; water;
DOI:10.1016/j.carres.2005.11.007