N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-(α,α-dimethyl-4-succin-monoamidobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

Base Information

Chemical Name:N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-(α,α-dimethyl-4-succin-monoamidobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester
CAS No.:301843-72-1
Molecular Formula:C₄₈H₆₁N₃O₁₃Si
Molecular Weight:916.11
Hs Code.:

N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-(α,α-dimethyl-4-succin-monoamidobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

Synonyms:N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-(α,α-dimethyl-4-succin-monoamidobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

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Chemical Property of N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-(α,α-dimethyl-4-succin-monoamidobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

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Technology Process of N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-(α,α-dimethyl-4-succin-monoamidobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

There total 14 articles about N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-(α,α-dimethyl-4-succin-monoamidobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl 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: 82.0%

: 108-30-5
succinic acid anhydride

: 301843-71-0
N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-(α,α-dimethyl-4-aminobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

: 301843-72-1
N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-(α,α-dimethyl-4-succin-monoamidobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

Guidance literature:: With 4-methyl-morpholine; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1016/S0040-4020(00)00588-3

Reference yield:

: (2S,3R)-3-((4aR,6S,7R,8R,8aR)-7-Azido-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid allyl ester

: 301843-72-1
N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-(α,α-dimethyl-4-succin-monoamidobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

Guidance literature:: Multi-step reaction with 9 steps

2: 97 percent

3: 365 mg / camphorsulfonic acid / acetonitrile / 5 h / 20 °C

4: Zn; AcOH / CH₂Cl₂ / 0.33 h / 20 °C

5: 336 mg / methanol / 0.5 h / 20 °C

6: 92 percent / AcOH; Bu₄NF / tetrahydrofuran / 4 h / 0 - 4 °C

7: 97 percent / NaI / dimethylformamide / 0.75 h / -20 °C

8: 94 percent / AcOH; Zn / tetrahydrofuran / 0.75 h / 20 °C

9: 82 percent / 4-methylmorpholine / CH₂Cl₂ / 3 h / 20 °C

With 4-methyl-morpholine; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; acetic acid; sodium iodide; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: debenzylidenation / 2: silylation / 3: Cyclization / 4: Reduction / 5: Acetylation / 6: desilylation / 7: silylation / 8: Reduction / 9: Acylation;
DOI:10.1016/S0040-4020(00)00588-3

Reference yield:

: 221325-35-5
chloro(α,α-dimethyl-4-nitrobenzyl)dimethylsilane

: 301843-72-1
N-(9-fluorenylmethoxycarbonyl)-O-[2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-(α,α-dimethyl-4-succin-monoamidobenzyl)dimethylsilyl-α-D-galactopyranosyl]-L-threonine allyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / NaI / dimethylformamide / 0.75 h / -20 °C

2: 94 percent / AcOH; Zn / tetrahydrofuran / 0.75 h / 20 °C

3: 82 percent / 4-methylmorpholine / CH₂Cl₂ / 3 h / 20 °C

With 4-methyl-morpholine; acetic acid; sodium iodide; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: silylation / 2: Reduction / 3: Acylation;
DOI:10.1016/S0040-4020(00)00588-3