1-(methoxycarbonyl)pentadec-10(S)-yl 3,4-O-isopropylidene-β-D-fucopyranoside

Base Information

Chemical Name:1-(methoxycarbonyl)pentadec-10(S)-yl 3,4-O-isopropylidene-β-D-fucopyranoside
CAS No.:180782-63-2
Molecular Formula:C₂₆H₄₈O₇
Molecular Weight:472.663
Hs Code.:

Synonyms:1-(methoxycarbonyl)pentadec-10(S)-yl 3,4-O-isopropylidene-β-D-fucopyranoside

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Chemical Property of 1-(methoxycarbonyl)pentadec-10(S)-yl 3,4-O-isopropylidene-β-D-fucopyranoside

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Technology Process of 1-(methoxycarbonyl)pentadec-10(S)-yl 3,4-O-isopropylidene-β-D-fucopyranoside

There total 1 articles about 1-(methoxycarbonyl)pentadec-10(S)-yl 3,4-O-isopropylidene-β-D-fucopyranoside 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:

: 55362-80-6
9-bromononan-1-ol

: 180782-63-2
1-(methoxycarbonyl)pentadec-10(S)-yl 3,4-O-isopropylidene-β-D-fucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: 97 percent / imidazole; DMAP / CH₂Cl₂ / 3 h / 20 °C

2.1: magnesium; I₂ / tetrahydrofuran / 2 h / Heating

2.2: 66 percent / CuI / tetrahydrofuran / 2.5 h / -78 - 20 °C

3.1: 90.5 percent / pyridine / 20 °C

4.1: 89.4 percent / Jones reagent / acetone / 1.5 h / 0 - 20 °C

5.1: 96.9 percent / BF₃*OEt₂ / 4 h / 40 °C

6.1: 65.7 percent / 4 Angstroem MS; BF₃*OEt₂ / CH₂Cl₂ / 1 h / -30 - 0 °C

7.1: NaOMe / methanol / 0.42 h / -15 °C

8.1: 154 mg / p-TsOH / acetone / 20 °C

With pyridine; 1H-imidazole; dmap; jones reagent; 4 Angstroem MS; boron trifluoride diethyl etherate; iodine; sodium methylate; toluene-4-sulfonic acid; magnesium; In tetrahydrofuran; methanol; dichloromethane; acetone; 1.1: silylation / 2.1: Metallation / 2.2: Addition / 3.1: Acetylation / 4.1: Jones oxidation / 5.1: methanolysis / 6.1: glycosylation / 7.1: Deacetylation / 8.1: Cyclization;
DOI:10.1021/jo9711450

Reference yield: 99.0%

: 1448686-56-3
2-O-acetyl-3-O-p-methoxybenzyl-4-O-tert-butyldimethylsilyl-α-L-rhamnopyranosyl trichloroacetimidate

: 180782-63-2
1-(methoxycarbonyl)pentadec-10(S)-yl 3,4-O-isopropylidene-β-D-fucopyranoside

: 1448686-58-5
1-(methoxycarbonyl)pentadec-10(S)-yl 2-O-acetyl-3-O-p-methoxybenzyl-4-O-tert-butyldimethylsilyl-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-β-D-fucopyranoside

Guidance literature:: 2-O-acetyl-3-O-p-methoxybenzyl-4-O-tert-butyldimethylsilyl-α-L-rhamnopyranosyl trichloroacetimidate; 1-(methoxycarbonyl)pentadec-10(S)-yl 3,4-O-isopropylidene-β-D-fucopyranoside; In dichloromethane; at 20 ℃; for 0.166667h; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 0 ℃; for 2h;
DOI:10.1021/ol4020255

Reference yield: 97.0%

: 2-O-chloroacetyl-3-O-p-methoxybenzyl-4-O-tertbutyldimethylsilyl-α-L-rhamnopyranosyl trichloroacetimidate

: 180782-63-2
1-(methoxycarbonyl)pentadec-10(S)-yl 3,4-O-isopropylidene-β-D-fucopyranoside

: 1-(methoxycarbonyl)pentadec-10(S)-yl 2-O-chloroacetyl-3-O-p-methoxybenzyl-4-O-tertbutyldimethylsilyl-α-L-rhamnopyranosyl-(1→2)-3,4-O-isopropylidene-β-D-fucopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 - 0 ℃; for 2h; Molecular sieve;
DOI:10.1080/10286020.2014.998653