4-methoxyphenyl 2-O-acetyl-3,6-di-O-benzyl-4-O-triisopropylsilyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-α-D-xylopyranoside

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Chemical Name:4-methoxyphenyl 2-O-acetyl-3,6-di-O-benzyl-4-O-triisopropylsilyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-α-D-xylopyranoside
CAS No.:1350309-51-1
Molecular Formula:C₅₇H₆₈O₁₄Si
Molecular Weight:1005.24
Hs Code.:

Synonyms:

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Chemical Property of 4-methoxyphenyl 2-O-acetyl-3,6-di-O-benzyl-4-O-triisopropylsilyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-α-D-xylopyranoside

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Technology Process of 4-methoxyphenyl 2-O-acetyl-3,6-di-O-benzyl-4-O-triisopropylsilyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-α-D-xylopyranoside

There total 21 articles about 4-methoxyphenyl 2-O-acetyl-3,6-di-O-benzyl-4-O-triisopropylsilyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-α-D-xylopyranoside 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:

: 62446-93-9
1,2,3,4-tetra-O-acetyl-D-xylopyranose

: 1350309-51-1
4-methoxyphenyl 2-O-acetyl-3,6-di-O-benzyl-4-O-triisopropylsilyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-α-D-xylopyranoside

Guidance literature:: Multi-step reaction with 12 steps

1: boron trifluoride diethyl etherate; triethylamine / dichloromethane / 24 h / 0 - 20 °C / Molecular sieve 4A

2: trimethylsilyl trifluoromethanesulfonate / chloroform-d1 / 26 h

3: sodium methylate / methanol / 16 h / 20 °C / Inert atmosphere

4: CSA / N,N-dimethyl-formamide / 18 h / 20 °C

5: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 0 - 20 °C / Inert atmosphere

6: pyridinium p-toluenesulfonate / isopropyl alcohol / 72 h / 20 °C / Inert atmosphere

7: pyridine; dmap / 1.5 h / 0 - 20 °C / Inert atmosphere

8: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere

9: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 0 - 20 °C / Molecular sieve 4A; Inert atmosphere

10: 2,6-di-tert-butyl-4-methylpyridine; methyl trifluoromethanesulfonate / dichloromethane / 20 h / 40 °C / Inert atmosphere; Molecular sieve 4A

11: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C

12: pyridine / 1 h / 20 °C

With pyridine; 1H-imidazole; dmap; 2,6-di-tert-butyl-4-methylpyridine; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; pyridinium p-toluenesulfonate; acetic acid; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; chloroform-d1; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/ja208528c

Reference yield:

: 1350309-53-3
methyl 4,6-O-benzylidene-2-O-(2-naphthylmethyl)-1-thio-3-O-triisopropylsilyl-α-D-mannopyranoside

: 1350309-51-1
4-methoxyphenyl 2-O-acetyl-3,6-di-O-benzyl-4-O-triisopropylsilyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-α-D-xylopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere

2: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere

3: triethylsilane; trifluoroacetic acid / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere

4: 2,6-dimethylpyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

5: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 0 - 20 °C / Molecular sieve 4A; Inert atmosphere

6: 2,6-di-tert-butyl-4-methylpyridine; methyl trifluoromethanesulfonate / dichloromethane / 20 h / 40 °C / Inert atmosphere; Molecular sieve 4A

7: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C

8: pyridine / 1 h / 20 °C

With pyridine; 2,6-dimethylpyridine; triethylsilane; 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; sodium hydride; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja208528c

Reference yield:

: 1350309-56-6
methyl 3,6-di-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

: 1350309-51-1
4-methoxyphenyl 2-O-acetyl-3,6-di-O-benzyl-4-O-triisopropylsilyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-α-D-xylopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 2,6-dimethylpyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / 0 - 20 °C / Molecular sieve 4A; Inert atmosphere

3: 2,6-di-tert-butyl-4-methylpyridine; methyl trifluoromethanesulfonate / dichloromethane / 20 h / 40 °C / Inert atmosphere; Molecular sieve 4A

4: trifluoroacetic acid / dichloromethane / 0.5 h / 0 °C

5: pyridine / 1 h / 20 °C

With pyridine; 2,6-dimethylpyridine; 2,6-di-tert-butyl-4-methylpyridine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; methyl trifluoromethanesulfonate; In dichloromethane;
DOI:10.1021/ja208528c