(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

Base Information

• Chemical Name: (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
• CAS No.: 245450-64-0
• Molecular Formula: C₄₀H₅₆O₁₀
• Molecular Weight: 696.879
• Mol file: 245450-64-0.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 13 articles about (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 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: 57.0%

benzyl bromide (100-39-0) + (2R,4aR,6S,7R,8R,8aS)-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]dioxine-7,8-diol (201542-27-0) → (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) + (2R,4aR,6S,7R,8S,8aS)-7-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-8-ol (245450-66-2)

Guidance literature:

(2R,4aR,6S,7R,8R,8aS)-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]dioxine-7,8-diol; With bis(tri-n-butyltin)oxide; In toluene; for 6h; Heating;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In toluene; for 2.5h;

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) → (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)

Guidance literature:

Multi-step reaction with 6 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

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;

DOI:10.1021/ja991361l

Reference yield:

hex-5-en-1-al (764-59-0) → (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)

Guidance literature:

Multi-step reaction with 7 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

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;

DOI:10.1021/ja991361l

upstream raw materials:

benzyl bromide

(2R,4aR,6S,7R,8R,8aS)-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]dioxine-7,8-diol

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

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