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

Base Information

• Chemical Name: 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
• CAS No.: 180782-75-6
• Molecular Formula: C₄₃H₆₆O₁₄
• Molecular Weight: 806.989
• Mol file: 180782-75-6.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 39 articles about 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 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: 84.0%

1-(methoxycarbonyl)pentadec-10(S)-yl 3,4-O-isopropylidene-β-D-fucopyranoside (180782-63-2) + 2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranose 1-trichloroacetimidate (180782-72-3) → 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)

Guidance literature:

With silver trifluoromethanesulfonate; In dichloromethane;

DOI:10.1021/jo960655b

Reference yield: 76.5%

1-(methoxycarbonyl)pentadec-10(S)-yl 3,4-O-isopropylidene-β-D-fucopyranoside (180782-63-2) + ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside (197853-38-6) → 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)

Guidance literature:

With N-iodo-succinimide; silver trifluoromethanesulfonate; In dichloromethane; at -15 ℃; for 0.5h;

DOI:10.1002/anie.199723441

Reference yield:

9-bromononan-1-ol (55362-80-6) → 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)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; 1H-imidazole; dmap; 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; 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;

DOI:10.1021/jo9711450

upstream raw materials:

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

2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranose 1-trichloroacetimidate

ethyl 2,3-di-O-acetyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside

benzyl α-D-fucopyranoside

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

methyl (11S)-11-[[(3-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoate

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

methyl (11S)-11-[[(4,6-O-benzylidene-β-D-glucopyranosyl)-(1->2)-3,4-O-isopropylidene-β-D-fucopyranosyl]oxy]hexadecanoate

Refernces

• 1、 Lu, Shou-Fu,O'yang, QinQin,Guo, Zhong-Wu,Yu, Biao,Hui, Yong-Zheng. "The First Total Synthesis of Tricolorin A". . p. 2344 - 2346. Retrieved 2007/10/03.
• 2、 Larson, Daniel P.,Heathcock, Clayton H.. "Synthesis of the macrolactone disaccharide subunit of tricolorin A". . p. 5208 - 5209. Retrieved 2007/10/03.