3-{(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-[(1R,2R)-2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-yl}-propionic acid methyl ester

Base Information

• Chemical Name: 3-{(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-[(1R,2R)-2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-yl}-propionic acid methyl ester
• CAS No.: 198828-40-9
• Molecular Formula: C₄₂H₅₄O₁₃
• Molecular Weight: 766.883

Synonyms:3-{(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-[(1R,2R)-2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-yl}-propionic acid methyl ester

Chemical Property of 3-{(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-[(1R,2R)-2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-yl}-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-[(1R,2R)-2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-yl}-propionic acid methyl ester

There total 11 articles about 3-{(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-[(1R,2R)-2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-yl}-propionic acid methyl 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: 100.0%

C70H70O17 (198828-32-9) → 3-{(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-[(1R,2R)-2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-yl}-propionic acid methyl ester (198828-40-9)

Guidance literature:

With sodium methylate; In methanol; Ambient temperature;

DOI:10.1016/S0960-894X(97)10041-5

Reference yield:

1,2,3,4,6-penta-O-acetyl-α,β-L-galactose (70749-17-6) → 3-{(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-[(1R,2R)-2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-yl}-propionic acid methyl ester (198828-40-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 55 percent / N₂H₄*HOAc / dimethylformamide / Ambient temperature

2: 1.) Cl₃CCN, Cs₂CO₃, 2.) Me₃SiOTf / 1.) CH₂Cl₂, room temperature, 2.) CH₂Cl₂, -20 deg C

3: 100 percent / NaOMe / methanol / Ambient temperature

4: 73 percent / pyridine, DMAP / Ambient temperature

5: 79 percent / NaH / dimethylformamide / Ambient temperature

6: 94 percent / aq. TFA / CH₂Cl₂ / Ambient temperature

7: 1.) (COCl)2, Et₃N / 1.) DMSO, -78 deg C -> room temperature, 2.) CH₂Cl₂, -20 deg C

8: 1.) H₂, 2.) TFA / 1.) PtO₂ / 1.) MeOH, 2.) CH₂Cl₂, 0 deg C

9: 1.) (COBr)2, 2.) nBu₄NBr, 4 Angstroem molecular sieves / 1.) CH₂Cl₂, DMF, 0 deg C, 2.) CH₂Cl₂, DMF, room temperature

10: 75 percent / 2>OTf, 4 Angstroem molecular sieves / CH₂Cl₂ / Ambient temperature

11: 100 percent / NaOMe / methanol / Ambient temperature

With pyridine; dmap; oxalyl dichloride; Oxalyl bromide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutylammomium bromide; hydrogen; sodium methylate; hydrazinium monoacetate; sodium hydride; caesium carbonate; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine; trichloroacetonitrile; trifluoroacetic acid; platinum(IV) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(97)10041-5

Reference yield:

Acetic acid (2S,3R,4R,5S)-3,5-diacetoxy-2-acetoxymethyl-6-hydroxy-tetrahydro-pyran-4-yl ester → 3-{(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-[(1R,2R)-2-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-yl}-propionic acid methyl ester (198828-40-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) Cl₃CCN, Cs₂CO₃, 2.) Me₃SiOTf / 1.) CH₂Cl₂, room temperature, 2.) CH₂Cl₂, -20 deg C

2: 100 percent / NaOMe / methanol / Ambient temperature

3: 73 percent / pyridine, DMAP / Ambient temperature

4: 79 percent / NaH / dimethylformamide / Ambient temperature

5: 94 percent / aq. TFA / CH₂Cl₂ / Ambient temperature

6: 1.) (COCl)2, Et₃N / 1.) DMSO, -78 deg C -> room temperature, 2.) CH₂Cl₂, -20 deg C

7: 1.) H₂, 2.) TFA / 1.) PtO₂ / 1.) MeOH, 2.) CH₂Cl₂, 0 deg C

8: 1.) (COBr)2, 2.) nBu₄NBr, 4 Angstroem molecular sieves / 1.) CH₂Cl₂, DMF, 0 deg C, 2.) CH₂Cl₂, DMF, room temperature

9: 75 percent / 2>OTf, 4 Angstroem molecular sieves / CH₂Cl₂ / Ambient temperature

10: 100 percent / NaOMe / methanol / Ambient temperature

With pyridine; dmap; oxalyl dichloride; Oxalyl bromide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutylammomium bromide; hydrogen; sodium methylate; sodium hydride; caesium carbonate; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine; trichloroacetonitrile; trifluoroacetic acid; platinum(IV) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(97)10041-5

upstream raw materials:

C₇₀H₇₀O₁₇

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

1,2,3,4,6-penta-O-acetyl-α,β-L-galactose

(2S,3S,4R,5S,6S)-2-Hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,4,5-triol

Downstream raw materials:

3-{(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-[(1R,2R)-2-((2S,4aR,6R,7R,8R,8aR)-7,8-dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-yl}-propionic acid methyl ester

3-{(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-[(1R,2R)-2-((2S,4aR,6R,7R,8R,8aR)-7,8-dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-yl}-propionic acid

3-{(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-[(1R,2R)-2-((2S,4aR,6R,7R,8R,8aR)-7,8-dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-cyclohexyloxy]-tetrahydro-pyran-2-yl}-propionic acid allyl ester

C₆₄H₆₈O₁₄

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