4-O-(tert-butyldimethylsilyl)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

Base Information

Chemical Name:4-O-(tert-butyldimethylsilyl)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside
CAS No.:1443651-40-8
Molecular Formula:C₃₉H₅₀O₉Si
Molecular Weight:690.906
Hs Code.:

Synonyms:4-O-(tert-butyldimethylsilyl)-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-(tert-butyldimethylsilyl)-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-(tert-butyldimethylsilyl)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

There total 9 articles about 4-O-(tert-butyldimethylsilyl)-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: 80.0%

: 1443651-39-5
C₂₅H₄₂O₇Si

: 98-88-4
benzoyl chloride

: 1443651-40-8
4-O-(tert-butyldimethylsilyl)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: With pyridine; In dichloromethane; Inert atmosphere;
DOI:10.1002/chem.201204545

Reference yield:

: 53270-14-7
benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

: 1443651-40-8
4-O-(tert-butyldimethylsilyl)-α-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere

2.1: acetic acid / 120 h / 20 °C / Inert atmosphere

3.1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h

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

5.2: Inert atmosphere

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

7.1: pyridine / dichloromethane / Inert atmosphere

With pyridine; lithium aluminium tetrahydride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/chem.201204545

Reference yield:

: 316157-01-4
benzyl 2,3-O-isopropylidene-4-O-(4-methoxybenzyl)-α-L-rhamnopyranoside

: 1443651-40-8
4-O-(tert-butyldimethylsilyl)-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: acetic acid / 120 h / 20 °C / Inert atmosphere

2.1: pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 3 h

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

4.2: Inert atmosphere

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

6.1: pyridine / dichloromethane / Inert atmosphere

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