(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

Base Information

• Chemical Name: (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
• CAS No.: 198828-35-2
• Molecular Formula: C₆₇H₇₄O₁₅
• Molecular Weight: 1119.32

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 17 articles about (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 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:

1,2,3,4,6-penta-O-acetyl-α,β-L-galactose (70749-17-6) → (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 (198828-35-2)

Guidance literature:

Multi-step reaction with 16 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

15: 1.) nBu₂SnO, 2.) CsF / 1.) benzene, reflux, 10 h, 2.) DME, room temperature

16: 1.) Dess-Martin periodinate, 2.) NaBH₄ / 1.) CH₂Cl₂, room temperature, 2.) iPrOH, 0 deg C

With pyridine; dmap; lithium hydroxide; sodium tetrahydroborate; oxalyl dichloride; Oxalyl bromide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutylammomium bromide; hydrogen; sodium methylate; hydrazinium monoacetate; sodium hydride; di(n-butyl)tin oxide; caesium carbonate; Dess-Martin periodane; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine; trichloroacetonitrile; cesium fluoride; 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 → (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 (198828-35-2)

Guidance literature:

Multi-step reaction with 15 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

14: 1.) nBu₂SnO, 2.) CsF / 1.) benzene, reflux, 10 h, 2.) DME, room temperature

15: 1.) Dess-Martin periodinate, 2.) NaBH₄ / 1.) CH₂Cl₂, room temperature, 2.) iPrOH, 0 deg C

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

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

Reference yield:

(2S,3S,4R,5S,6S)-2-Hydroxymethyl-6-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-3,4,5-triol (198828-37-4) → (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 (198828-35-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 73 percent / pyridine, DMAP / Ambient temperature

2: 79 percent / NaH / dimethylformamide / Ambient temperature

3: 94 percent / aq. TFA / CH₂Cl₂ / Ambient temperature

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

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

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

7: 75 percent / 2>OTf, 4 Angstroem molecular sieves / CH₂Cl₂ / Ambient temperature

8: 100 percent / NaOMe / methanol / Ambient temperature

9: 88 percent / CSA / acetonitrile / Ambient temperature

10: 95 percent / aq. LiOH / ethanol / 60 °C

11: 87 percent / Cs₂CO₃ / Ambient temperature

12: 1.) nBu₂SnO, 2.) CsF / 1.) benzene, reflux, 10 h, 2.) DME, room temperature

13: 1.) Dess-Martin periodinate, 2.) NaBH₄ / 1.) CH₂Cl₂, room temperature, 2.) iPrOH, 0 deg C

With pyridine; dmap; lithium hydroxide; sodium tetrahydroborate; oxalyl dichloride; Oxalyl bromide; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutylammomium bromide; hydrogen; sodium methylate; sodium hydride; di(n-butyl)tin oxide; caesium carbonate; Dess-Martin periodane; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; triethylamine; cesium fluoride; 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:

(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

(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:

C₆₄H₆₈O₁₄

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