(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester

Base Information

• Chemical Name: (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester
• CAS No.: 215028-97-0
• Molecular Formula: C₃₈H₄₈N₄O₉Si
• Molecular Weight: 732.906

Synonyms:(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester

Chemical Property of (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester

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Technology Process of (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester

There total 4 articles about (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester 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:

N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester (73724-48-8) → (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester (215028-97-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Cp₂ZrCl₂, AgOTf / CH₂Cl₂

2: I₂, MeOH

3: imidazole / dimethylformamide

With 1H-imidazole; methanol; zirconocene dichloride; iodine; silver trifluoromethanesulfonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja9825128

Reference yield:

(2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Azido-2,2-dimethyl-4-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester (213331-76-1) → (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester (215028-97-0)

Guidance literature:

Multi-step reaction with 2 steps

1: I₂, MeOH

2: imidazole / dimethylformamide

With 1H-imidazole; methanol; iodine; In N,N-dimethyl-formamide;

DOI:10.1021/ja9825128

Reference yield:

((3aR,4R,7R,7aR)-7-Azido-6-fluoro-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy)-triisopropyl-silane → (2S,3R)-3-[(2S,3R,4R,5R,6R)-3-Azido-6-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-tetrahydro-pyran-2-yloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester (215028-97-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Cp₂ZrCl₂, AgOTf / CH₂Cl₂

2: I₂, MeOH

3: imidazole / dimethylformamide

With 1H-imidazole; methanol; zirconocene dichloride; iodine; silver trifluoromethanesulfonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja9825128

upstream raw materials:

tert-butyldimethylsilyl chloride

N^α-fluoren-9-ylmethoxycarbonyl-O-(2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester

N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester

(2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Azido-2,2-dimethyl-4-triisopropylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester

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