Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-3-C-methyl-β-D-arabino-hexofuranoside

Base Information

Chemical Name:Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-3-C-methyl-β-D-arabino-hexofuranoside
CAS No.:161606-82-2
Molecular Formula:C₂₄H₃₄O₄Si
Molecular Weight:414.617
Hs Code.:

Synonyms:Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-3-C-methyl-β-D-arabino-hexofuranoside

Suppliers and Price of Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-3-C-methyl-β-D-arabino-hexofuranoside

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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-3-C-methyl-β-D-arabino-hexofuranoside

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-3-C-methyl-β-D-arabino-hexofuranoside

There total 11 articles about Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-3-C-methyl-β-D-arabino-hexofuranoside 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: 20.0%

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

: 2(R,S)-<2(R)-<(Diphenyl-tert-butylsilyl)oxy>ethyl>-3H-4,5-dihydrofuran-3-one

: 161606-82-2
Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-3-C-methyl-β-D-arabino-hexofuranoside

Guidance literature:: With methylmagnesium chloride; In tetrahydrofuran; at -20 ℃; for 0.166667h;
DOI:10.1021/jo00106a035

Reference yield: 12.0%

: 676-58-4
methylmagnesium chloride

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

: 2(R,S)-<2(R)-<(Diphenyl-tert-butylsilyl)oxy>ethyl>-3H-4,5-dihydrofuran-3-one

: 161606-82-2
Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-3-C-methyl-β-D-arabino-hexofuranoside

Guidance literature:: In tetrahydrofuran; at -20 ℃; for 0.166667h;
DOI:10.1021/jo00106a035

Reference yield:

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

: 161606-82-2
Methyl 5-O-(tert-butyldiphenylsilyl)-2,6-dideoxy-3-C-methyl-β-D-arabino-hexofuranoside

Guidance literature:: Multi-step reaction with 7 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

7: 1.) CeCl₃ / 1.) THF, sonication, 0 deg C, 1 h; Et₂O, -75 deg C, 1 h, 2.) THF, 10 min

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