Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-β-D-erythro-hexofuranosid-3-ulose

Base Information

Chemical Name:Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-β-D-erythro-hexofuranosid-3-ulose
CAS No.:161606-80-0
Molecular Formula:C₂₃H₃₀O₄Si
Molecular Weight:398.574
Hs Code.:

Synonyms:Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-β-D-erythro-hexofuranosid-3-ulose

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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 Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-β-D-erythro-hexofuranosid-3-ulose

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Technology Process of Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-β-D-erythro-hexofuranosid-3-ulose

There total 8 articles about Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-β-D-erythro-hexofuranosid-3-ulose 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: 90.0%

: 161606-79-7
Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-β-D-ribo-hexofuranoside

: 161606-80-0
Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-β-D-erythro-hexofuranosid-3-ulose

Guidance literature:: With pyridine; chromium(VI) oxide; acetic anhydride; In dichloromethane; 1.) 20 deg C, 15 min, 2.) 15 min;
DOI:10.1021/jo00106a035

Reference yield:

: 113666-60-7
methyl 2-deoxy-3-O-benzyl-β-D-erythro-pentofuranoside

: 161606-80-0
Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-β-D-erythro-hexofuranosid-3-ulose

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) (COCl)2, DMSO, 2.) NEt₃ / 1.) CH₂Cl₂, ca. -50 deg C, 15 min, 2.) ca. -50 deg C to 20 deg C

2: diethyl ether / -70 °C

3: 99 percent / pyridine, imidazole / 17 h / 20 °C

4: NBS, aq. CaCO₃ / CCl₄ / 0.5 h / 20 - 25 °C / Irradiation

5: KOH / methanol / 18 h / Ambient temperature

6: 90 percent / CrO₃, pyridine, Ac₂O / CH₂Cl₂ / 1.) 20 deg C, 15 min, 2.) 15 min

With pyridine; 1H-imidazole; chromium(VI) oxide; potassium hydroxide; N-Bromosuccinimide; oxalyl dichloride; acetic anhydride; dimethyl sulfoxide; triethylamine; calcium carbonate; In methanol; tetrachloromethane; diethyl ether; dichloromethane;
DOI:10.1021/jo00106a035

Reference yield:

: 105454-48-6
3-O-Benzyl-2-deoxy-5-(triphenylmethyl)-D-erythro-pentofuranoside

: 161606-80-0
Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-β-D-erythro-hexofuranosid-3-ulose

Guidance literature:: Multi-step reaction with 7 steps

1: methanolic HCl / 3.5 h / 20 °C

2: 1.) (COCl)2, DMSO, 2.) NEt₃ / 1.) CH₂Cl₂, ca. -50 deg C, 15 min, 2.) ca. -50 deg C to 20 deg C

3: diethyl ether / -70 °C

4: 99 percent / pyridine, imidazole / 17 h / 20 °C

5: NBS, aq. CaCO₃ / CCl₄ / 0.5 h / 20 - 25 °C / Irradiation

6: KOH / methanol / 18 h / Ambient temperature

7: 90 percent / CrO₃, pyridine, Ac₂O / CH₂Cl₂ / 1.) 20 deg C, 15 min, 2.) 15 min

With pyridine; 1H-imidazole; chromium(VI) oxide; hydrogenchloride; potassium hydroxide; N-Bromosuccinimide; oxalyl dichloride; acetic anhydride; dimethyl sulfoxide; triethylamine; calcium carbonate; In methanol; tetrachloromethane; diethyl ether; dichloromethane;
DOI:10.1021/jo00106a035