allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-acetyl-3-O-benzyl-6-O-thexyldimethylsilyl-α-L-idopyranoside

Base Information

Chemical Name:allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-acetyl-3-O-benzyl-6-O-thexyldimethylsilyl-α-L-idopyranoside
CAS No.:245109-98-2
Molecular Formula:C₄₈H₆₅N₃O₁₂Si
Molecular Weight:904.143
Hs Code.:

Synonyms:allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-acetyl-3-O-benzyl-6-O-thexyldimethylsilyl-α-L-idopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-acetyl-3-O-benzyl-6-O-thexyldimethylsilyl-α-L-idopyranoside

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Technology Process of allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-acetyl-3-O-benzyl-6-O-thexyldimethylsilyl-α-L-idopyranoside

There total 8 articles about allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-acetyl-3-O-benzyl-6-O-thexyldimethylsilyl-α-L-idopyranoside 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: 83.0%

: 154970-28-2
6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate

: allyl 2-O-acetyl-3-O-benzyl-6-O-thexyldimethylsilyl-α-L-idopyranoside

: 245109-98-2
allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-acetyl-3-O-benzyl-6-O-thexyldimethylsilyl-α-L-idopyranoside

Guidance literature:: With t-butyldimethylsiyl triflate; In dichloromethane; toluene; at -20 ℃; for 0.5h;
DOI:10.1016/S0040-4020(99)00526-8

Reference yield:

: 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranose

: 245109-98-2
allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-acetyl-3-O-benzyl-6-O-thexyldimethylsilyl-α-L-idopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: imidazole / dimethylformamide / 20 h

2: MeONa / methanol / 3 h

3: NaH / dimethylformamide

4: AcOH; ZnCl₂ / 4 h / 20 °C

5: Bu₄NF; AcOH / tetrahydrofuran / 25 h

6: 10 percent / K₂CO₃ / CH₂Cl₂ / 20 h

7: 83 percent / tert-butyldimethylsilyl triflate / toluene; CH₂Cl₂ / 0.5 h / -20 °C

With 1H-imidazole; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; potassium carbonate; acetic acid; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: silylation / 2: Deacetylation / 3: Alkylation / 4: debenzylation-acetylation / 5: desilylation / 6: Addition / 7: Condensation;
DOI:10.1016/S0040-4020(99)00526-8

Reference yield:

: 171032-74-9
1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

: 245109-98-2
allyl (6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-2-O-acetyl-3-O-benzyl-6-O-thexyldimethylsilyl-α-L-idopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: NH₃ / tetrahydrofuran; methanol / 0 °C

2: imidazole / dimethylformamide / 20 h

3: MeONa / methanol / 3 h

4: NaH / dimethylformamide

5: AcOH; ZnCl₂ / 4 h / 20 °C

6: Bu₄NF; AcOH / tetrahydrofuran / 25 h

7: 10 percent / K₂CO₃ / CH₂Cl₂ / 20 h

8: 83 percent / tert-butyldimethylsilyl triflate / toluene; CH₂Cl₂ / 0.5 h / -20 °C

With 1H-imidazole; t-butyldimethylsiyl triflate; tetrabutyl ammonium fluoride; ammonia; sodium methylate; sodium hydride; potassium carbonate; acetic acid; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Deacetylation / 2: silylation / 3: Deacetylation / 4: Alkylation / 5: debenzylation-acetylation / 6: desilylation / 7: Addition / 8: Condensation;
DOI:10.1016/S0040-4020(99)00526-8