phenyl [[[[(3-azido-2,3-dideoxy-4-trimethylsilyl-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-3-azido-2,3-dideoxy-1-thio-α-...

Base Information

• Chemical Name: phenyl [[[[(3-azido-2,3-dideoxy-4-trimethylsilyl-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-3-azido-2,3-dideoxy-1-thio-α-...
• CAS No.: 264626-95-1
• Molecular Formula: C₃₉H₅₉N₁₅O₁₀SSi
• Molecular Weight: 958.143

Synonyms:phenyl [[[[(3-azido-2,3-dideoxy-4-trimethylsilyl-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-3-azido-2,3-dideoxy-1-thio-α-...

Chemical Property of phenyl [[[[(3-azido-2,3-dideoxy-4-trimethylsilyl-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-3-azido-2,3-dideoxy-1-thio-α-...

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Technology Process of phenyl [[[[(3-azido-2,3-dideoxy-4-trimethylsilyl-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-3-azido-2,3-dideoxy-1-thio-α-...

There total 12 articles about phenyl [[[[(3-azido-2,3-dideoxy-4-trimethylsilyl-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-3-azido-2,3-dideoxy-1-thio-α-... 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: 74.0%

[(2S,3S,4S,6S)-4-Azido-6-((2S,3S,4S,6S)-4-azido-6-benzenesulfinyl-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-trimethyl-silane (264626-94-0) + phenyl [[(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-3-azido-2,3-dideoxy-1-thio-α-L-fucopyranoside (264626-93-9) → phenyl [[[[(3-azido-2,3-dideoxy-4-trimethylsilyl-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-3-azido-2,3-dideoxy-1-thio-α-... (264626-95-1)

Guidance literature:

With trifluoromethylsulfonic anhydride; 4 A molecular sieve; In diethyl ether; dichloromethane; at -78 ℃; for 0.25h;

DOI:10.1021/ja992513f

Reference yield:

4-O-acetyl-3-azido-2,3,6-trideoxy-L-ribo-hexopyranose → phenyl [[[[(3-azido-2,3-dideoxy-4-trimethylsilyl-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-3-azido-2,3-dideoxy-1-thio-α-... (264626-95-1)

Guidance literature:

Multi-step reaction with 11 steps

1: pyridine; DMAP / 0.33 h / 20 °C

2: BF₃*Et₂O / CH₂Cl₂ / 0.33 h / 20 °C

3: K₂CO₃ / methanol / 2 h / 20 °C

4: pyridine / CH₂Cl₂ / 1 h

5: 18-crown-6 / dimethylformamide / 4 h

6: LiOH / methanol

7: Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

8: mCPBA / CH₂Cl₂ / -42 °C

9: 21 percent / 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves; triflic anhydride / toluene; CH₂Cl₂ / 0.25 h / -78 °C

10: 95 percent / pyridinium hydrofluoride / tetrahydrofuran

11: 74 percent / triflic anhydride; 4 Angstroem molecular sieves / CH₂Cl₂; diethyl ether / 0.25 h / -78 °C

With pyridine; dmap; lithium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; 18-crown-6 ether; trifluoromethylsulfonic anhydride; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium carbonate; pyridine hydrogenfluoride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Acetylation / 2: Substitution / 3: Hydrolysis / 4: sulphonation / 5: Esterification / 6: Hydrolysis / 7: silylation / 8: Oxidation / 9: Condensation / 10: desilylation / 11: Condensation;

DOI:10.1021/ja992513f

Reference yield:

(2S,3R,4S,6S)-4-Azido-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol (283170-20-7) → phenyl [[[[(3-azido-2,3-dideoxy-4-trimethylsilyl-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-3-azido-2,3-dideoxy-1-thio-α-... (264626-95-1)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine / CH₂Cl₂ / 1 h

2: 18-crown-6 / dimethylformamide / 4 h

3: LiOH / methanol

4: Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

5: mCPBA / CH₂Cl₂ / -42 °C

6: 21 percent / 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem molecular sieves; triflic anhydride / toluene; CH₂Cl₂ / 0.25 h / -78 °C

7: 95 percent / pyridinium hydrofluoride / tetrahydrofuran

8: 74 percent / triflic anhydride; 4 Angstroem molecular sieves / CH₂Cl₂; diethyl ether / 0.25 h / -78 °C

With pyridine; lithium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; 18-crown-6 ether; trifluoromethylsulfonic anhydride; 4 A molecular sieve; pyridine hydrogenfluoride; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 1: sulphonation / 2: Esterification / 3: Hydrolysis / 4: silylation / 5: Oxidation / 6: Condensation / 7: desilylation / 8: Condensation;

DOI:10.1021/ja992513f

upstream raw materials:

[(2S,3S,4S,6S)-4-Azido-6-((2S,3S,4S,6S)-4-azido-6-benzenesulfinyl-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-trimethyl-silane

phenyl [[(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-(3-azido-2,3-dideoxy-α-L-fucopyranosyl)]-(1-4)-3-azido-2,3-dideoxy-1-thio-α-L-fucopyranoside

(2S,3S,4S,6S)-4-Azido-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

(2S,3R,4S,6S)-4-Azido-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

Downstream raw materials:

C₃₇H₅₃N₁₅O₁₀S

4-azido-6-(4-azido-6-{4-azido-6-[4-azido-6-(4-azido-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3-yloxy}-2-methyl-tetrahydro-pyran-3-yloxy)-2-methyl-tetrahydro-pyran-3-ol

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