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

Base Information

Chemical Name:(2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Azido-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester
CAS No.:213331-79-4
Molecular Formula:C₃₅H₃₈N₄O₉
Molecular Weight:658.708
Hs Code.:

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

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

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

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

There total 8 articles about (2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Azido-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-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: 94.0%

: 213331-76-1
(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

: 213331-79-4
(2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Azido-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 72h; Ambient temperature;
DOI:10.1021/ja980724z

Reference yield:

: 73724-48-8
N-(fluoren-9-ylmethoxycarbonyl)-L-threonine benzyl ester

: 213331-79-4
(2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Azido-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: Cp₂ZrCl₂, AgOTf / CH₂Cl₂

2: TBAF, AcOH / tetrahydrofuran

With zirconocene dichloride; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; acetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja9825128

Reference yield:

: (3aR,4R,7R,7aR)-7-azido-2,2-dimethyl-4-(((triisopropylsilyl)oxy)methyl)tetrahydro-4H-[1,3]dioxolo[4,5-c]pyran-6-ol

: 213331-79-4
(2S,3R)-3-((3aR,4R,6S,7R,7aR)-7-Azido-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 70 percent / K₂CO₃ / CH₂Cl₂ / 5 h / 0 - 20 °C

2: 29 percent / TMSOTf, 4A molecular sieves / CH₂Cl₂ / 4.5 h / -78 - 20 °C

3: 94 percent / HOAc, TBAF / tetrahydrofuran / 72 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja980724z