allyl 2-azido-2-deoxy-3-O-benzyl-6-O-tertbutyldiphenylsilyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranosyl)]-β-D-glucopyranoside

Base Information

Chemical Name:allyl 2-azido-2-deoxy-3-O-benzyl-6-O-tertbutyldiphenylsilyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranosyl)]-β-D-glucopyranoside
CAS No.:647027-51-8
Molecular Formula:C₇₂H₇₇N₃O₁₄Si
Molecular Weight:1236.5
Hs Code.:

allyl 2-azido-2-deoxy-3-O-benzyl-6-O-tertbutyldiphenylsilyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranosyl)]-β-D-glucopyranoside

Synonyms:allyl 2-azido-2-deoxy-3-O-benzyl-6-O-tertbutyldiphenylsilyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranosyl)]-β-D-glucopyranoside

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Chemical Property of allyl 2-azido-2-deoxy-3-O-benzyl-6-O-tertbutyldiphenylsilyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranosyl)]-β-D-glucopyranoside

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Technology Process of allyl 2-azido-2-deoxy-3-O-benzyl-6-O-tertbutyldiphenylsilyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranosyl)]-β-D-glucopyranoside

There total 6 articles about allyl 2-azido-2-deoxy-3-O-benzyl-6-O-tertbutyldiphenylsilyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranosyl)]-β-D-glucopyranoside 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: 85.0%

: (2R,3S,4R,5R,6R)-6-Allyloxy-5-azido-4-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3-ol

: O-(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α,β-L-idopyranosyl) trichloroacetimidate

: 647027-51-8
allyl 2-azido-2-deoxy-3-O-benzyl-6-O-tertbutyldiphenylsilyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranosyl)]-β-D-glucopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -75 - 20 ℃;
DOI:10.1021/ol0359261

Reference yield:

: 123-76-2
levulinic acid

: 647027-51-8
allyl 2-azido-2-deoxy-3-O-benzyl-6-O-tertbutyldiphenylsilyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranosyl)]-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 8 h / 20 °C

2: 82 percent / tris(triphenylphosphine)rhodium(I) chloride / toluene; ethanol; H₂O / 15 h / Heating

3: 95 percent / sodium hydride / CH₂Cl₂ / 0.5 h / 0 °C

4: 85 percent / trimethylsilyl trifluoromethanesulfonate; molecular sieves 4 Angstroem / CH₂Cl₂ / -75 - 20 °C

With dmap; Wilkinson's catalyst; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium hydride; dicyclohexyl-carbodiimide; In ethanol; dichloromethane; water; toluene;
DOI:10.1021/ol0359261

Reference yield:

: 647027-46-1
allyl 3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-α-L-idopyranoside

: 647027-51-8
allyl 2-azido-2-deoxy-3-O-benzyl-6-O-tertbutyldiphenylsilyl-4-O-[(3,6-di-O-benzyl-4-O-(9-fluorenylmethoxycarbonyl)-2-O-levulinoyl-α-L-idopyranosyl)]-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 8 h / 20 °C

2: 82 percent / tris(triphenylphosphine)rhodium(I) chloride / toluene; ethanol; H₂O / 15 h / Heating

3: 95 percent / sodium hydride / CH₂Cl₂ / 0.5 h / 0 °C

4: 85 percent / trimethylsilyl trifluoromethanesulfonate; molecular sieves 4 Angstroem / CH₂Cl₂ / -75 - 20 °C

With dmap; Wilkinson's catalyst; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium hydride; dicyclohexyl-carbodiimide; In ethanol; dichloromethane; water; toluene;
DOI:10.1021/ol0359261