N-(9-fluorenylmethyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine phenacylester

Base Information

Chemical Name:N-(9-fluorenylmethyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine phenacylester
CAS No.:125762-71-2
Molecular Formula:C₃₉H₄₀N₄O₁₃
Molecular Weight:772.766
Hs Code.:

Synonyms:N-(9-fluorenylmethyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine phenacylester

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Chemical Property of N-(9-fluorenylmethyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine phenacylester

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Technology Process of N-(9-fluorenylmethyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine phenacylester

There total 3 articles about N-(9-fluorenylmethyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine phenacylester 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:

: 68733-05-1
3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl nitrate

: 125762-71-2
N-(9-fluorenylmethyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine phenacylester

Guidance literature:: Multi-step reaction with 3 steps

1: 55 percent / 18-crown-6 / CH₂Cl₂ / 50 h / Ambient temperature

2: 59 percent / NaI / acetone / 17 h / Heating

3: N-iodosuccinimide, molecular sieves, TfOH / CH₂Cl₂ / 6 h / -10 °C

With N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; sodium iodide; 18-crown-6 ether; In dichloromethane; acetone;
DOI:10.1002/prac.19973390160

Reference yield:

: 125760-27-2
N-(9-fluorenylmethyloxycarbonyl)-L-threonine phenacylester

: 191341-67-0
Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-pent-4-enylsulfanyl-tetrahydro-pyran-4-yl ester

: N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl)-L-threonine phenacyl ester

: 125762-71-2
N-(9-fluorenylmethyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine phenacylester

Guidance literature:: With N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; In dichloromethane; at -10 ℃; for 6h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1002/prac.19973390160

Reference yield:

: 191341-66-9
Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-azido-6-pent-4-enyloxythiocarbonylsulfanyl-tetrahydro-pyran-4-yl ester

: 125762-71-2
N-(9-fluorenylmethyloxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-L-threonine phenacylester

Guidance literature:: Multi-step reaction with 2 steps

1: 59 percent / NaI / acetone / 17 h / Heating

2: N-iodosuccinimide, molecular sieves, TfOH / CH₂Cl₂ / 6 h / -10 °C

With N-iodo-succinimide; molecular sieve; trifluorormethanesulfonic acid; sodium iodide; In dichloromethane; acetone;
DOI:10.1002/prac.19973390160