(3R,4R,5S,6R)-2-heptadecyl-tetrahydro-2-hydroxy-4,5-O-isopropylidene-6-tert-butyldiphenylsilyloxy-methyl-2H-pyran-3-yl acetate

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Chemical Name:(3R,4R,5S,6R)-2-heptadecyl-tetrahydro-2-hydroxy-4,5-O-isopropylidene-6-tert-butyldiphenylsilyloxy-methyl-2H-pyran-3-yl acetate
CAS No.:352219-97-7
Molecular Formula:C₄₄H₇₀O₇Si
Molecular Weight:739.121
Hs Code.:

Synonyms:(3R,4R,5S,6R)-2-heptadecyl-tetrahydro-2-hydroxy-4,5-O-isopropylidene-6-tert-butyldiphenylsilyloxy-methyl-2H-pyran-3-yl acetate

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Chemical Property of (3R,4R,5S,6R)-2-heptadecyl-tetrahydro-2-hydroxy-4,5-O-isopropylidene-6-tert-butyldiphenylsilyloxy-methyl-2H-pyran-3-yl acetate

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Technology Process of (3R,4R,5S,6R)-2-heptadecyl-tetrahydro-2-hydroxy-4,5-O-isopropylidene-6-tert-butyldiphenylsilyloxy-methyl-2H-pyran-3-yl acetate

There total 6 articles about (3R,4R,5S,6R)-2-heptadecyl-tetrahydro-2-hydroxy-4,5-O-isopropylidene-6-tert-butyldiphenylsilyloxy-methyl-2H-pyran-3-yl acetate 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: 95.0%

: 108-24-7
acetic anhydride

: 352219-96-6
(3R,4R,5S,6R)-2-heptadecyl-tetrahydro-4,5-O-isopropylidene-6-tert-butyldiphenylsilyloxy-methyl-2H-pyran-2,3-diol

: 352219-97-7
(3R,4R,5S,6R)-2-heptadecyl-tetrahydro-2-hydroxy-4,5-O-isopropylidene-6-tert-butyldiphenylsilyloxy-methyl-2H-pyran-3-yl acetate

Guidance literature:: With dmap; In ethyl acetate; at 20 ℃; for 0.0833333h;
DOI:10.1016/j.bmc.2005.09.044

Reference yield:

: 224324-95-2
tert-butyl-(6-heptadecyl-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy)-diphenyl-silane

: 352219-97-7
(3R,4R,5S,6R)-2-heptadecyl-tetrahydro-2-hydroxy-4,5-O-isopropylidene-6-tert-butyldiphenylsilyloxy-methyl-2H-pyran-3-yl acetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: osmium tetroxide; N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; H₂O; acetone / 0.5 h / 20 °C

1.2: 80 percent / sodium bisulfite / 2-methyl-propan-2-ol; H₂O; acetone / 0.5 h

2.1: 95 percent / DMAP / ethyl acetate / 0.08 h / 20 °C

With dmap; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; ethyl acetate; acetone; tert-butyl alcohol;
DOI:10.1016/j.bmc.2005.09.044

Reference yield:

: (R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-((S)-2,2-dimethyl-5-phenylsulfanyl-[1,3]dioxolan-4-yl)-ethanol

: 352219-97-7
(3R,4R,5S,6R)-2-heptadecyl-tetrahydro-2-hydroxy-4,5-O-isopropylidene-6-tert-butyldiphenylsilyloxy-methyl-2H-pyran-3-yl acetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 92 percent / DCC; DMAP / benzene / 2 h / 20 °C

2.1: 99 percent / pyridine / toluene; tetrahydrofuran / 1.25 h / 0 - 20 °C

3.1: 87 percent / 2,6-di-tert-butyl-4-methylpyridine; molecular sieves 4 Angstroem; methyl triflate / CH₂Cl₂ / 24 h / 20 °C

4.1: osmium tetroxide; N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; H₂O; acetone / 0.5 h / 20 °C

4.2: 80 percent / sodium bisulfite / 2-methyl-propan-2-ol; H₂O; acetone / 0.5 h

5.1: 95 percent / DMAP / ethyl acetate / 0.08 h / 20 °C

With pyridine; dmap; osmium(VIII) oxide; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide; methyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone; toluene; tert-butyl alcohol; benzene;
DOI:10.1016/j.bmc.2005.09.044