N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-xylopyranosyl)-L-serine benzyl ester

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Chemical Name:N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-xylopyranosyl)-L-serine benzyl ester
CAS No.:1415218-12-0
Molecular Formula:C₅₀H₅₃NO₁₁Si
Molecular Weight:872.056
Hs Code.:

Synonyms:N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-xylopyranosyl)-L-serine benzyl ester

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Chemical Property of N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-xylopyranosyl)-L-serine benzyl ester

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Technology Process of N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-xylopyranosyl)-L-serine benzyl ester

There total 19 articles about N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-xylopyranosyl)-L-serine 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: 83.0%

: 1426447-50-8
p-tolyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-xylopyranoside

: 118358-66-0,73724-46-6
N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester

: 1415218-12-0
N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-xylopyranosyl)-L-serine benzyl ester

Guidance literature:: p-tolyl 2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-1-thio-β-D-xylopyranoside; With silver trifluoromethanesulfonate; In diethyl ether; dichloromethane; at -78 ℃; for 0.0833333h; Inert atmosphere; Molecular sieve;

With para-thiocresol; In diethyl ether; dichloromethane; at -78 ℃; for 0.0833333h; Inert atmosphere;

N-(9-fluorenylmethyloxycarbonyl)-L-serine benzyl ester; With 2,4,6-tri-tert-butylpyrimidine; In diethyl ether; dichloromethane; at -78 - 0 ℃; for 2h; Inert atmosphere;
DOI:10.1002/anie.201205601

Reference yield:

: 73724-45-5
N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine

: 1415218-12-0
N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-xylopyranosyl)-L-serine benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium hydrogencarbonate; tetra-(n-butyl)ammonium iodide / dimethyl sulfoxide / 8 h / 20 °C / Inert atmosphere

2.1: silver trifluoromethanesulfonate / dichloromethane; diethyl ether / 0.08 h / -78 °C / Inert atmosphere; Molecular sieve

2.2: 0.08 h / -78 °C / Inert atmosphere

2.3: 2 h / -78 - 0 °C / Inert atmosphere

With silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydrogencarbonate; In diethyl ether; dichloromethane; dimethyl sulfoxide;
DOI:10.1002/anie.201205601

Reference yield:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
D-Xylose

: 1415218-12-0
N-fluorenylmethyloxycarbonyl-O-(2,3-di-O-benzoyl-4-O-tert-butyldimethylsilyl-β-D-xylopyranosyl)-L-serine benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: pyridine / 20 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 20 h / 20 °C / Inert atmosphere

3.1: sodium methylate / dichloromethane; methanol / 20 °C / pH 12 / Inert atmosphere

3.2: pH 7 / Inert atmosphere

4.1: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 2 h / 60 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 20 °C / Inert atmosphere

6.1: camphor-10-sulfonic acid / dichloromethane; methanol / 20 °C / Inert atmosphere

7.1: dmap / dichloromethane / Inert atmosphere; Reflux

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 20 °C / Inert atmosphere

9.1: 2,6-dimethylpyridine / dichloromethane / -40 - 20 °C / Inert atmosphere

10.1: silver trifluoromethanesulfonate / dichloromethane; diethyl ether / 0.08 h / -78 °C / Inert atmosphere; Molecular sieve

10.2: 0.08 h / -78 °C / Inert atmosphere

10.3: 2 h / -78 - 0 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; dmap; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/anie.201205601