6-(7-acetylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid

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Chemical Name:6-(7-acetylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid
CAS No.:273749-68-1
Molecular Formula:C₅₀H₆₀N₂O₂₀
Molecular Weight:1009.03
Hs Code.:

6-(7-acetylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-<i>d</i>][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid

Synonyms:6-(7-acetylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid

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Chemical Property of 6-(7-acetylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid

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Technology Process of 6-(7-acetylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid

There total 19 articles about 6-(7-acetylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid 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:

: acetic acid 3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[6-(7-acetylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-4-yl ester

: 273749-68-1
6-(7-acetylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutylammomium bromide; In dichloromethane; water; at 0 ℃; for 0.333333h;
DOI:10.1021/ol0057075

Reference yield:

: (2R,3S,4R)-5-Azido-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3,4-diol

: 273749-68-1
6-(7-acetylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 11 steps

1.1: 424 mg / p-TsOH*H₂O / acetonitrile / 6 h / 20 °C

2.1: 83 percent / Tf₂O; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -60 - -30 °C

3.1: 442 mg / LiOH*H₂O / methanol; tetrahydrofuran; H₂O / 24 h / 60 °C

4.1: NaH / dimethylformamide; various solvent(s)

4.2: 82 percent / dimethylformamide; various solvent(s) / 6 h / 0 °C

5.1: 91 percent / NaBH₃CN; TFA; 3 Angstroem molecular sieves / dimethylformamide / 8 h / 0 °C

6.1: 86 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 0 - 20 °C

7.1: Cd / dimethylformamide; acetic acid / 8 h / 20 °C

8.1: thioacetic acid / pyridine / 12 h / 20 °C

9.1: 288 mg / pyridine / 0.5 h

10.1: cerium(IV) ammonium nitrate / CH₂Cl₂; H₂O / 1 h / 0 °C

11.1: TEMPO; NaOCl; TBABr / CH₂Cl₂; H₂O / 0.33 h / 0 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; sodium hypochlorite; 2,6-di-tert-butyl-4-methylpyridine; ammonium cerium(IV) nitrate; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; tetrabutylammomium bromide; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; tiolacetic acid; cadmium; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile; 1.1: Deacetylation / 2.1: Condensation / 3.1: Hydrolysis / 4.1: Metallation / 4.2: Benzylation / 5.1: Reduction / 6.1: Condensation / 7.1: Reduction / 8.1: Reduction / 9.1: Acetylation / 10.1: Substitution / 11.1: Oxidation;
DOI:10.1021/ol0057075

Reference yield:

: phenyl 2,3-di-O-pivaloyl-4,6-O-(4-methoxybenzylidene)-1-thio-β-D-glucopyranosyl sulfoxide

: 273749-68-1
6-(7-acetylamino-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-4,5-bis-benzyloxy-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

1.1: 83 percent / Tf₂O; 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / -60 - -30 °C

2.1: 442 mg / LiOH*H₂O / methanol; tetrahydrofuran; H₂O / 24 h / 60 °C

3.1: NaH / dimethylformamide; various solvent(s)

3.2: 82 percent / dimethylformamide; various solvent(s) / 6 h / 0 °C

4.1: 91 percent / NaBH₃CN; TFA; 3 Angstroem molecular sieves / dimethylformamide / 8 h / 0 °C

5.1: 86 percent / TMSOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 3 h / 0 - 20 °C

6.1: Cd / dimethylformamide; acetic acid / 8 h / 20 °C

7.1: thioacetic acid / pyridine / 12 h / 20 °C

8.1: 288 mg / pyridine / 0.5 h

9.1: cerium(IV) ammonium nitrate / CH₂Cl₂; H₂O / 1 h / 0 °C

10.1: TEMPO; NaOCl; TBABr / CH₂Cl₂; H₂O / 0.33 h / 0 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; sodium hypochlorite; 2,6-di-tert-butyl-4-methylpyridine; ammonium cerium(IV) nitrate; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; 4 A molecular sieve; tetrabutylammomium bromide; sodium hydride; sodium cyanoborohydride; trifluoroacetic acid; tiolacetic acid; cadmium; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 1.1: Condensation / 2.1: Hydrolysis / 3.1: Metallation / 3.2: Benzylation / 4.1: Reduction / 5.1: Condensation / 6.1: Reduction / 7.1: Reduction / 8.1: Acetylation / 9.1: Substitution / 10.1: Oxidation;
DOI:10.1021/ol0057075