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}-ethanol

Base Information

• Chemical Name: 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}-ethanol
• CAS No.: 188636-75-1
• Molecular Formula: C₅₅H₆₄O₁₂
• Molecular Weight: 917.106
• Mol file: 188636-75-1.mol

Synonyms: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}-ethanol

Chemical Property of 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}-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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}-ethanol

There total 7 articles about 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}-ethanol 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: 83.0%

(2S,4aR,6R,7R,8S,8aS)-7-(2-Allyloxy-ethoxy)-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]dioxine (188636-73-9) → 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}-ethanol (188636-75-1)

Guidance literature:

With Wilkinson's catalyst; In ethanol; water; for 3h; Heating;

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-{(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}-ethanol (188636-75-1)

Guidance literature:

Multi-step reaction with 7 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

With Wilkinson's catalyst; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutylammomium bromide; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; 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-{(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}-ethanol (188636-75-1)

Guidance literature:

Multi-step reaction with 7 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

With Wilkinson's catalyst; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutylammomium bromide; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; 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)-7-(2-Allyloxy-ethoxy)-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]dioxine

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

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

(2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol

Downstream raw materials:

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

(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