2-(2-{(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-ethyl)-malonic acid dimethyl ester

Base Information

• Chemical Name: 2-(2-{(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-ethyl)-malonic acid dimethyl ester
• CAS No.: 188636-79-5
• Molecular Formula: C₆₀H₇₀O₁₅
• Molecular Weight: 1031.21
• Mol file: 188636-79-5.mol

Synonyms:2-(2-{(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-ethyl)-malonic acid dimethyl ester

Chemical Property of 2-(2-{(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-ethyl)-malonic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(2-{(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-ethyl)-malonic acid dimethyl ester

There total 10 articles about 2-(2-{(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-ethyl)-malonic acid dimethyl 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: 92.0%

(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(2-bromo-ethoxy)-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxine (188636-77-3) + malonic acid dimethyl ester (108-59-8) → 2-(2-{(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-ethyl)-malonic acid dimethyl ester (188636-79-5)

Guidance literature:

With dibenzo-18-crown-6; potassium carbonate; at 95 ℃; for 5h;

DOI:10.1016/S0040-4020(96)01178-7

Reference yield:

(1R,2R)-trans-1,2-cyclohexanediol (1072-86-2,1460-57-7,1792-81-0,54383-22-1,57794-08-8,931-17-9) → 2-(2-{(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-ethyl)-malonic acid dimethyl ester (188636-79-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 72 percent / trimethylsilyl-trifluoromethanesulfonate / CH₂Cl₂; diethyl ether / 1 h

2: 95 percent / tetrabutylammonium bromide, molecular sieves 4 Angstroem, copper(II) bromide / CH₂Cl₂; dimethylformamide / 24 h

3: 98 percent / NaOMe / methanol / 3 h

4: 1.) dibutyltin oxide, 2.) tetrabutylammonium iodide / 1) methanol, reflux, 18 h; 2) toluene, 45 deg C, 17 h

5: 89 percent / p-toluenesulfonic acid / acetonitrile / 1 h

6: 1.) NaH / 1) DMF, 1 h; 2) DMF, 18 h

7: 83 percent / Wilkinson catalyst / ethanol; H₂O / 3 h / Heating

8: 95 percent / Ph₃P, Et₃N, 1,2-dibromo-tetrachloroethane / CH₂Cl₂ / 2 h

9: 92 percent / potassium carbonate, dibenzo-18-crown-6 / 5 h / 95 °C

With Wilkinson's catalyst; dibenzo-18-crown-6; 1,2-dibromo-1,1,2,2-tetrachloroethane; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutylammomium bromide; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; copper(ll) bromide; In methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(96)01178-7

Reference yield:

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,142831-80-9,127061-80-7) → 2-(2-{(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy}-ethyl)-malonic acid dimethyl ester (188636-79-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 72 percent / trimethylsilyl-trifluoromethanesulfonate / CH₂Cl₂; diethyl ether / 1 h

2: 95 percent / tetrabutylammonium bromide, molecular sieves 4 Angstroem, copper(II) bromide / CH₂Cl₂; dimethylformamide / 24 h

3: 98 percent / NaOMe / methanol / 3 h

4: 1.) dibutyltin oxide, 2.) tetrabutylammonium iodide / 1) methanol, reflux, 18 h; 2) toluene, 45 deg C, 17 h

5: 89 percent / p-toluenesulfonic acid / acetonitrile / 1 h

6: 1.) NaH / 1) DMF, 1 h; 2) DMF, 18 h

7: 83 percent / Wilkinson catalyst / ethanol; H₂O / 3 h / Heating

8: 95 percent / Ph₃P, Et₃N, 1,2-dibromo-tetrachloroethane / CH₂Cl₂ / 2 h

9: 92 percent / potassium carbonate, dibenzo-18-crown-6 / 5 h / 95 °C

With Wilkinson's catalyst; dibenzo-18-crown-6; 1,2-dibromo-1,1,2,2-tetrachloroethane; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutylammomium bromide; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; copper(ll) bromide; In methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(96)01178-7

upstream raw materials:

(2S,4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(2-bromo-ethoxy)-2-phenyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-hexahydro-pyrano[3,2-d][1,3]dioxine

malonic acid dimethyl ester

(1R,2R)-trans-1,2-cyclohexanediol

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate