acetic acid 4,5-bis-benzyloxy-2-{8-benzyloxy-2-phenyl-6-[2,2,4-trimethyl-6-(1-pentyl-hex-5-enyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: acetic acid 4,5-bis-benzyloxy-2-{8-benzyloxy-2-phenyl-6-[2,2,4-trimethyl-6-(1-pentyl-hex-5-enyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 245450-68-4
• Molecular Formula: C₆₂H₈₀O₁₅
• Molecular Weight: 1065.31
• Mol file: 245450-68-4.mol

Synonyms:acetic acid 4,5-bis-benzyloxy-2-{8-benzyloxy-2-phenyl-6-[2,2,4-trimethyl-6-(1-pentyl-hex-5-enyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of acetic acid 4,5-bis-benzyloxy-2-{8-benzyloxy-2-phenyl-6-[2,2,4-trimethyl-6-(1-pentyl-hex-5-enyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of acetic acid 4,5-bis-benzyloxy-2-{8-benzyloxy-2-phenyl-6-[2,2,4-trimethyl-6-(1-pentyl-hex-5-enyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-6-methyl-tetrahydro-pyran-3-yl ester

There total 17 articles about acetic acid 4,5-bis-benzyloxy-2-{8-benzyloxy-2-phenyl-6-[2,2,4-trimethyl-6-(1-pentyl-hex-5-enyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-6-methyl-tetrahydro-pyran-3-yl 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: 53.0%

2-O-acetyl-3,4-di-O-benzyl-1-(2,2,2-trichloroethanimidate)-α/β-L-rhamnopyranoside (686767-31-7) + (2R,4aR,6S,7R,8R,8aR)-8-Benzyloxy-2-phenyl-6-[(3aS,4R,6R,7R,7aS)-2,2,4-trimethyl-6-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (245450-64-0) → acetic acid 4,5-bis-benzyloxy-2-{8-benzyloxy-2-phenyl-6-[2,2,4-trimethyl-6-(1-pentyl-hex-5-enyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-6-methyl-tetrahydro-pyran-3-yl ester (245450-68-4)

Guidance literature:

With boron trifluoride diethyl etherate; In hexane; dichloromethane; at -20 ℃; for 1h;

DOI:10.1021/ja991361l

Reference yield:

2,3,4-tri-O-acetyl-D-fucopyranosyl bromide (5158-64-5,14227-85-1,16741-27-8,24877-07-4,36807-84-8,39524-38-4,41881-45-2,60978-06-5,69483-13-2,69980-52-5,75247-28-8,75247-29-9,80483-13-2,80483-14-3,89301-86-0,96648-29-2,108942-35-4,108942-38-7,138514-69-9,24404-52-2) → acetic acid 4,5-bis-benzyloxy-2-{8-benzyloxy-2-phenyl-6-[2,2,4-trimethyl-6-(1-pentyl-hex-5-enyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-6-methyl-tetrahydro-pyran-3-yl ester (245450-68-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: AgNO₃; silica/alumina; 3 Angstroem molecular sieves / CH₂Cl₂ / -10 °C

2.1: KOMe; MeOH / 20 °C

3.1: p-TsOH*H₂O / acetone

4.1: 82 percent / BF₃*Et₂O / CH₂Cl₂; hexane / -20 °C

5.1: 71 percent / KOMe; MeOH / 20 °C

6.1: (n-Bu₃Sn)2O / toluene / 6 h / Heating

6.2: 57 percent / Bu₄NI / toluene / 2.5 h

7.1: 53 percent / BF₃*Et₂O / CH₂Cl₂; hexane / 1 h / -20 °C

With methanol; aluminum oxide; 3 A molecular sieve; boron trifluoride diethyl etherate; potassium methanolate; silica gel; toluene-4-sulfonic acid; silver nitrate; bis(tri-n-butyltin)oxide; In hexane; dichloromethane; acetone; toluene; 1.1: Condensation / 2.1: Deacetylation / 3.1: Cycloaddition / 4.1: Condensation / 5.1: Deacetylation / 6.1: Etherification / 6.2: benzylation / 7.1: Condensation;

DOI:10.1021/ja991361l

Reference yield:

hex-5-en-1-al (764-59-0) → acetic acid 4,5-bis-benzyloxy-2-{8-benzyloxy-2-phenyl-6-[2,2,4-trimethyl-6-(1-pentyl-hex-5-enyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-6-methyl-tetrahydro-pyran-3-yl ester (245450-68-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 86 percent / 1,2-cyclohexyl-bis(R,R-trifluoromethanesulfonamide); Ti(O-iPr)4 / toluene / 20 °C

2.1: AgNO₃; silica/alumina; 3 Angstroem molecular sieves / CH₂Cl₂ / -10 °C

3.1: KOMe; MeOH / 20 °C

4.1: p-TsOH*H₂O / acetone

5.1: 82 percent / BF₃*Et₂O / CH₂Cl₂; hexane / -20 °C

6.1: 71 percent / KOMe; MeOH / 20 °C

7.1: (n-Bu₃Sn)2O / toluene / 6 h / Heating

7.2: 57 percent / Bu₄NI / toluene / 2.5 h

8.1: 53 percent / BF₃*Et₂O / CH₂Cl₂; hexane / 1 h / -20 °C

With titanium(IV) isopropylate; methanol; aluminum oxide; 3 A molecular sieve; boron trifluoride diethyl etherate; potassium methanolate; silica gel; N,N’-(1R,2R)-cyclohexane-1,2-diylbis(1,1,1-trifluoromethanesulfonamide); toluene-4-sulfonic acid; silver nitrate; bis(tri-n-butyltin)oxide; In hexane; dichloromethane; acetone; toluene; 1.1: Addition / 2.1: Condensation / 3.1: Deacetylation / 4.1: Cycloaddition / 5.1: Condensation / 6.1: Deacetylation / 7.1: Etherification / 7.2: benzylation / 8.1: Condensation;

DOI:10.1021/ja991361l

upstream raw materials:

2-O-acetyl-3,4-di-O-benzyl-1-(2,2,2-trichloroethanimidate)-α/β-L-rhamnopyranoside

(2R,4aR,6S,7R,8R,8aR)-8-Benzyloxy-2-phenyl-6-[(3aS,4R,6R,7R,7aS)-2,2,4-trimethyl-6-((S)-1-pentyl-hex-5-enyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

2,3,4-tri-O-acetyl-D-fucopyranosyl bromide

hex-5-en-1-al

Downstream raw materials:

hept-6-enoic acid 4,5-bis-benzyloxy-2-{8-benzyloxy-2-phenyl-6-[2,2,4-trimethyl-6-(1-pentyl-hex-5-enyloxy)-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-6-methyl-tetrahydro-pyran-3-yl ester