phenyl 3-O-tert-butyldimethylsilyl-6-deoxy-4-O-methyl-1-thio-α-L-glucopyranoside

Base Information

Chemical Name:phenyl 3-O-tert-butyldimethylsilyl-6-deoxy-4-O-methyl-1-thio-α-L-glucopyranoside
CAS No.:400737-69-1
Molecular Formula:C₁₉H₃₂O₄SSi
Molecular Weight:384.612
Hs Code.:

Synonyms:phenyl 3-O-tert-butyldimethylsilyl-6-deoxy-4-O-methyl-1-thio-α-L-glucopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of phenyl 3-O-tert-butyldimethylsilyl-6-deoxy-4-O-methyl-1-thio-α-L-glucopyranoside

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Technology Process of phenyl 3-O-tert-butyldimethylsilyl-6-deoxy-4-O-methyl-1-thio-α-L-glucopyranoside

There total 7 articles about phenyl 3-O-tert-butyldimethylsilyl-6-deoxy-4-O-methyl-1-thio-α-L-glucopyranoside 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: 97.0%

: 400737-65-7
phenyl 3-O-tert-butyldimethylsilyl-4-O-methyl-2-oxo-1-thio-α-L-rhamnopyranoside

: 400737-69-1
phenyl 3-O-tert-butyldimethylsilyl-6-deoxy-4-O-methyl-1-thio-α-L-glucopyranoside

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.25h;
DOI:10.1002/anie.200460172

Reference yield:

: 131087-35-9
phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

: 400737-69-1
phenyl 3-O-tert-butyldimethylsilyl-6-deoxy-4-O-methyl-1-thio-α-L-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / KOH / dimethylformamide / 2 h / 0 °C

2: 89 percent / p-TsOH / dimethylformamide / 6 h / 20 °C

3: 91 percent / imidazole; DMAP / CH₂Cl₂; toluene / 16 h / 20 °C

4: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

5: NaBH₄ / methanol / 0.08 h / 0 °C

With 1H-imidazole; dmap; potassium hydroxide; sodium tetrahydroborate; Dess-Martin periodane; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4: Dess-Martin oxidation;
DOI:10.1002/chem.200600462

Reference yield:

: 400737-58-8
phenyl 2,3-O-isopropyliden-4-O-methyl-1-thio-α-L-rhamnopyranoside

: 400737-69-1
phenyl 3-O-tert-butyldimethylsilyl-6-deoxy-4-O-methyl-1-thio-α-L-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 89 percent / p-TsOH / dimethylformamide / 6 h / 20 °C

2: 91 percent / imidazole; DMAP / CH₂Cl₂; toluene / 16 h / 20 °C

3: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

4: NaBH₄ / methanol / 0.08 h / 0 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; Dess-Martin periodane; toluene-4-sulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 3: Dess-Martin oxidation;
DOI:10.1002/chem.200600462