C₇₀H₇₀O₁₇

Base Information

• Chemical Name: C₇₀H₇₀O₁₇
• CAS No.: 198828-32-9
• Molecular Formula: C₇₀H₇₀O₁₇
• Molecular Weight: 1183.32

Synonyms:C₇₀H₇₀O₁₇

Chemical Property of C₇₀H₇₀O₁₇

Chemical Property:

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Technology Process of C₇₀H₇₀O₁₇

There total 11 articles about C₇₀H₇₀O₁₇ 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: 75.0%

ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside (105376-04-3,113214-71-4,138661-53-7) + 3-[(2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-6-((1R,2R)-2-hydroxy-cyclohexyloxy)-tetrahydro-pyran-2-yl]-propionic acid methyl ester (198828-31-8) → C70H70O17 (198828-32-9)

Guidance literature:

With 4 A molecular sieve; dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In dichloromethane; 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) → C70H70O17 (198828-32-9)

Guidance literature:

Multi-step reaction with 10 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

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 → C70H70O17 (198828-32-9)

Guidance literature:

Multi-step reaction with 9 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

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:

ethyl 2,3,4,6-tetra-O-benzoyl-1-thio-β-D-galactopyranoside

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

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

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

Downstream 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

(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

C₆₄H₆₈O₁₄

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

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