1-(hydroxycarbonyl)pentadec-10(S)-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside

Base Information

• Chemical Name: 1-(hydroxycarbonyl)pentadec-10(S)-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside
• CAS No.: 180782-78-9
• Molecular Formula: C₃₈H₆₀O₁₂
• Molecular Weight: 708.887
• Mol file: 180782-78-9.mol

Synonyms:1-(hydroxycarbonyl)pentadec-10(S)-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside

Chemical Property of 1-(hydroxycarbonyl)pentadec-10(S)-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(hydroxycarbonyl)pentadec-10(S)-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside

There total 39 articles about 1-(hydroxycarbonyl)pentadec-10(S)-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-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: 91.0%

1-(methoxycarbonyl)pentadec-10(S)-yl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside (180782-75-6) → 1-(hydroxycarbonyl)pentadec-10(S)-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside (180782-78-9)

Guidance literature:

With potassium hydroxide; In methanol; water; for 10h; Heating;

DOI:10.1021/jo9711450

Reference yield:

9-bromononan-1-ol (55362-80-6) → 1-(hydroxycarbonyl)pentadec-10(S)-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside (180782-78-9)

Guidance literature:

Multi-step reaction with 10 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

9.1: 76.5 percent / 4 Angstroem MS; NIS; AgOTf / CH₂Cl₂; toluene / 0.5 h / -15 °C

10.1: 91 percent / KOH / methanol; H₂O / 10 h / Heating

With pyridine; 1H-imidazole; dmap; potassium hydroxide; N-iodo-succinimide; jones reagent; 4 Angstroem MS; boron trifluoride diethyl etherate; iodine; sodium methylate; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; magnesium; In tetrahydrofuran; methanol; dichloromethane; water; acetone; toluene; 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 / 9.1: glycosylation / 10.1: Hydrolysis;

DOI:10.1021/jo9711450

Reference yield:

benzyl α-D-fucopyranoside (127000-09-3) → 1-(hydroxycarbonyl)pentadec-10(S)-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside (180782-78-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 87 percent / p-TsOH*H₂O / acetone / 19 h

2: 96 percent / pyridine / 18 h / 70 °C

3: 84 percent / H₂ / Pd(OH)2 / ethyl acetate / 120 h / 2585.74 Torr

4: Cs₂CO₃ / CH₂Cl₂ / 12 h

5: 79 percent / TMSOTf / CH₂Cl₂ / 0.92 h

6: 96 percent / NaOMe / methanol; methyl acetate / 10 h

7: 84 percent / AgOTf / CH₂Cl₂ / 40 h

8: 74 percent / aq. LiOH / tetrahydrofuran / 15 h

With pyridine; lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; silver trifluoromethanesulfonate; caesium carbonate; toluene-4-sulfonic acid; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; acetic acid methyl ester; ethyl acetate; acetone; 1: Cyclization / 2: Acylation / 3: Hydrogenolysis / 4: Addition / 5: glycosylation / 6: deacylation / 7: glycosylation / 8: Hydrolysis;

DOI:10.1021/jo971413u

upstream raw materials:

1-(methoxycarbonyl)pentadec-10(S)-yl O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside

benzyl α-D-fucopyranoside

1-iodononane

9-bromononan-1-ol

Downstream raw materials:

(S)-1-(hydroxycarbonyl)pentadec-10-yl O-(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranoside 1,3-(B)-lactone