4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-β-D-glycopyranosyl-(1→4)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

Base Information

Chemical Name:4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-β-D-glycopyranosyl-(1→4)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside
CAS No.:1443651-64-6
Molecular Formula:C₆₀H₇₂O₁₆S₂Si
Molecular Weight:1141.44
Hs Code.:

4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-β-D-glycopyranosyl-(1→4)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

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Chemical Property of 4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-β-D-glycopyranosyl-(1→4)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

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Technology Process of 4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-β-D-glycopyranosyl-(1→4)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

There total 11 articles about 4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-β-D-glycopyranosyl-(1→4)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-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:

: 1443651-41-9
α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

: 142865-94-9
4-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-thiophenyl-6-O-p-toluenesulfonyl-1-trichloroacetimido-α-D-glucopyranose

: 1443651-64-6
4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-β-D-glycopyranosyl-(1→4)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

: 1443651-65-7
4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-α-D-glycopyranosyl-(1→4)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside; 4-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-thiophenyl-6-O-p-toluenesulfonyl-1-trichloroacetimido-α-D-glucopyranose; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 2h; Molecular sieve; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 - 20 ℃; Overall yield = 95 %; Overall yield = 244 mg; Molecular sieve; Inert atmosphere;
DOI:10.1002/chem.201204545

Reference yield:

: 1443651-39-5
C₂₅H₄₂O₇Si

: 1443651-64-6
4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-β-D-glycopyranosyl-(1→4)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

: 1443651-65-7
4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-α-D-glycopyranosyl-(1→4)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine / dichloromethane / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere

3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -78 °C / Molecular sieve; Inert atmosphere

3.2: -78 - 20 °C / Molecular sieve; Inert atmosphere

With pyridine; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;
DOI:10.1002/chem.201204545

Reference yield:

: 1443651-33-9
C₂₂H₂₄O₇

: 1443651-64-6
4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-β-D-glycopyranosyl-(1→4)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

: 1443651-65-7
4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-α-D-glycopyranosyl-(1→4)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h

2.1: lithium aluminium tetrahydride / 1,4-dioxane / 120 h / Inert atmosphere; Reflux

2.2: Inert atmosphere

3.1: potassium carbonate / methanol / 3 h / Inert atmosphere

4.1: pyridine / dichloromethane / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere

6.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -78 °C / Molecular sieve; Inert atmosphere

6.2: -78 - 20 °C / Molecular sieve; Inert atmosphere

With pyridine; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;
DOI:10.1002/chem.201204545