4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-β-D-glycopyranosyl-(1→4)-β-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)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside
• CAS No.: 1443651-62-4
• Molecular Formula: C₆₀H₇₂O₁₆S₂Si
• Molecular Weight: 1141.44

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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

There total 14 articles about 4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-β-D-glycopyranosyl-(1→4)-β-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:

β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside (1443651-54-4) + 4-O-acetyl-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-thiophenyl-6-O-p-toluenesulfonyl-1-trichloroacetimido-α-D-glucopyranose (142865-94-9) → 4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-β-D-glycopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside (1443651-62-4) + 4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-α-D-glycopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside (1443651-63-5)

Guidance literature:

β-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 diethyl ether; dichloromethane; at -78 ℃; Molecular sieve; Inert atmosphere;

With triethylamine; In diethyl ether; dichloromethane; at -78 - 20 ℃; Overall yield = 88 %; Overall yield = 1.59 g; Molecular sieve; Inert atmosphere;

DOI:10.1002/chem.201204545

Reference yield:

C22H24O7 (1443651-33-9) → 4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-β-D-glycopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside (1443651-62-4) + 4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-α-D-glycopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside (1443651-63-5)

Guidance literature:

Multi-step reaction with 9 steps

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

2.1: diethylzinc / tetrahydrofuran / 4 h / Molecular sieve; Inert atmosphere

2.2: Inert atmosphere; Molecular sieve

3.1: potassium carbonate / methanol / Inert atmosphere

4.1: pyridine / dichloromethane / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / Inert atmosphere

6.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

7.1: methanol; triethylamine / Inert atmosphere

8.1: toluene-4-sulfonic acid hydrazide; sodium acetate / water; 1,2-dimethoxyethane / 6 h / Reflux

9.1: trimethylsilyl trifluoromethanesulfonate / diethyl ether; dichloromethane / -78 °C / Molecular sieve; Inert atmosphere

9.2: -78 - 20 °C / Molecular sieve; Inert atmosphere

With pyridine; methanol; trimethylsilyl trifluoromethanesulfonate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; diethylzinc; sodium acetate; potassium carbonate; triethylamine; toluene-4-sulfonic acid hydrazide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; 6.1: |Mitsunobu Displacement;

DOI:10.1002/chem.201204545

Reference yield:

benzyl 2,3-O-carboxy-α-L-rhamnopyranoside (1443651-34-0) → 4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-β-D-glycopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside (1443651-62-4) + 4-O-acetyl-3-O-tert-butyldimethylsilyl-2-thiophenyl-6-O-tosyl-α-D-glycopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-benzyl-α-L-rhamnopyranoside (1443651-63-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: diethylzinc / tetrahydrofuran / 4 h / Molecular sieve; Inert atmosphere

1.2: Inert atmosphere; Molecular sieve

2.1: potassium carbonate / methanol / Inert atmosphere

3.1: pyridine / dichloromethane / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / Inert atmosphere

5.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

6.1: methanol; triethylamine / Inert atmosphere

7.1: toluene-4-sulfonic acid hydrazide; sodium acetate / water; 1,2-dimethoxyethane / 6 h / Reflux

8.1: trimethylsilyl trifluoromethanesulfonate / diethyl ether; dichloromethane / -78 °C / Molecular sieve; Inert atmosphere

8.2: -78 - 20 °C / Molecular sieve; Inert atmosphere

With pyridine; methanol; trimethylsilyl trifluoromethanesulfonate; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; diethylzinc; sodium acetate; potassium carbonate; triethylamine; toluene-4-sulfonic acid hydrazide; triphenylphosphine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; water; 5.1: |Mitsunobu Displacement;

DOI:10.1002/chem.201204545

upstream raw materials:

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

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

benzyl 4-O-(4-methoxybenzyl)-α-L-rhamnopyranoside

C₂₂H₂₄O₇

Downstream raw materials:

C₅₃H₆₅IO₁₃SSi

4-O-acetyl-3-O-tert-butyldimethylsilyl-β-D-olivopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-α-L-rhamnopyranoside

4-O-acetyl-3-O-tert-butyldimethylsilyl-β-D-olivopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-β-L-rhamnopyranoside

4-O-acetyl-3-O-tert-butyldimethylsilyl-β-D-olivopyranosyl-(1→4)-β-L-rhodinopyranosyl-(1→4)-2,3-di-O-benzoyl-1-O-trichloroacetimidate-β-L-rhamnopyranoside

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