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

Base Information

• Chemical Name: 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
• CAS No.: 198828-33-0
• Molecular Formula: C₅₁H₆₀O₁₃
• Molecular Weight: 881.03

Synonyms:

Chemical Property of 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

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-((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

There total 15 articles about 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 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: 87.0%

allyl bromide (106-95-6) + 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 (198828-42-1) → 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 (198828-33-0)

Guidance literature:

With caesium carbonate; 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-((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 (198828-33-0)

Guidance literature:

Multi-step reaction with 14 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

12: 88 percent / CSA / acetonitrile / Ambient temperature

13: 95 percent / aq. LiOH / ethanol / 60 °C

14: 87 percent / Cs₂CO₃ / Ambient temperature

With pyridine; dmap; lithium hydroxide; oxalyl dichloride; Oxalyl bromide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutylammomium bromide; hydrogen; sodium methylate; hydrazinium monoacetate; sodium hydride; caesium carbonate; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine; trichloroacetonitrile; trifluoroacetic acid; platinum(IV) oxide; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

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-((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 (198828-33-0)

Guidance literature:

Multi-step reaction with 13 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

11: 88 percent / CSA / acetonitrile / Ambient temperature

12: 95 percent / aq. LiOH / ethanol / 60 °C

13: 87 percent / Cs₂CO₃ / Ambient temperature

With pyridine; dmap; lithium hydroxide; oxalyl dichloride; Oxalyl bromide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutylammomium bromide; hydrogen; sodium methylate; sodium hydride; caesium carbonate; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine; trichloroacetonitrile; trifluoroacetic acid; platinum(IV) oxide; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

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

upstream raw materials:

allyl bromide

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

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

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

Downstream raw materials:

C₆₄H₆₈O₁₄

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

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

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