C₆₄H₆₈O₁₄

Base Information

• Chemical Name: C₆₄H₆₈O₁₄
• CAS No.: 198828-43-2
• Molecular Formula: C₆₄H₆₈O₁₄
• Molecular Weight: 1061.24

Synonyms:C₆₄H₆₈O₁₄

Chemical Property of C₆₄H₆₈O₁₄

Chemical Property:

Purity/Quality:

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Technology Process of C₆₄H₆₈O₁₄

There total 19 articles about C₆₄H₆₈O₁₄ 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) → C64H68O14 (198828-43-2)

Guidance literature:

Multi-step reaction with 18 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

17: Pd(PPh₃)4, morpholine / tetrahydrofuran

18: 1.) trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 2.) benzene, reflux, 24 h

With morpholine; pyridine; dmap; lithium hydroxide; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; Oxalyl bromide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; trichlorobenzoyl chloride; 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 tetrahydrofuran; 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 → C64H68O14 (198828-43-2)

Guidance literature:

Multi-step reaction with 17 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

16: Pd(PPh₃)4, morpholine / tetrahydrofuran

17: 1.) trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 2.) benzene, reflux, 24 h

With morpholine; pyridine; dmap; lithium hydroxide; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; Oxalyl bromide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; trichlorobenzoyl chloride; 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 tetrahydrofuran; 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) → C64H68O14 (198828-43-2)

Guidance literature:

Multi-step reaction with 15 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

14: Pd(PPh₃)4, morpholine / tetrahydrofuran

15: 1.) trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 2.) benzene, reflux, 24 h

With morpholine; pyridine; dmap; lithium hydroxide; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; Oxalyl bromide; 4 A molecular sieve; trichlorobenzoyl chloride; 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 tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

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

upstream raw materials:

(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

2-trimethylsilylethyl 2,3,4,6-tetra-O-acetyl-β-L-galactopyranoside

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