(1S)-2-acetyl-1,5-dideoxy-1-C-heptadecyl-3,4-O-isopropylidene-6-O-tert-butyldiphenysilyl-1,5-imino-D-galactitol

Base Information

Chemical Name:(1S)-2-acetyl-1,5-dideoxy-1-C-heptadecyl-3,4-O-isopropylidene-6-O-tert-butyldiphenysilyl-1,5-imino-D-galactitol
CAS No.:352219-99-9
Molecular Formula:C₄₄H₇₁NO₅Si
Molecular Weight:722.137
Hs Code.:

Synonyms:(1S)-2-acetyl-1,5-dideoxy-1-C-heptadecyl-3,4-O-isopropylidene-6-O-tert-butyldiphenysilyl-1,5-imino-D-galactitol

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Chemical Property of (1S)-2-acetyl-1,5-dideoxy-1-C-heptadecyl-3,4-O-isopropylidene-6-O-tert-butyldiphenysilyl-1,5-imino-D-galactitol

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Technology Process of (1S)-2-acetyl-1,5-dideoxy-1-C-heptadecyl-3,4-O-isopropylidene-6-O-tert-butyldiphenysilyl-1,5-imino-D-galactitol

There total 8 articles about (1S)-2-acetyl-1,5-dideoxy-1-C-heptadecyl-3,4-O-isopropylidene-6-O-tert-butyldiphenysilyl-1,5-imino-D-galactitol 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: 72.0%

: 352219-98-8
(3R,4S,5R)-3,4-O-isopropylidene-1-tert-butyldiphenylsilyloxy-2,6-dioxotricosan-5-yl acetate

: 352219-99-9
(1S)-2-acetyl-1,5-dideoxy-1-C-heptadecyl-3,4-O-isopropylidene-6-O-tert-butyldiphenysilyl-1,5-imino-D-galactitol

Guidance literature:: With 4 A molecular sieve; ammonium formate; sodium cyanoborohydride; In methanol; at 20 ℃; for 0.5h;
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

: 352219-99-9
(1S)-2-acetyl-1,5-dideoxy-1-C-heptadecyl-3,4-O-isopropylidene-6-O-tert-butyldiphenysilyl-1,5-imino-D-galactitol

Guidance literature:: Multi-step reaction with 4 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

3.1: 82 percent / PCC; florisil; sodium acetate / molecular sieves 4 Angstroem; Celite / CH₂Cl₂ / 3 h / 20 °C

4.1: 72 percent / sodium cyanoborohydride; ammonium formate; molecular sieves 4 Angstroem / methanol / 0.5 h / 20 °C

With dmap; florisil; osmium(VIII) oxide; 4 A molecular sieve; sodium acetate; ammonium formate; sodium cyanoborohydride; 4-methylmorpholine N-oxide; pyridinium chlorochromate; 4 A molecular sieve; Celite; In methanol; dichloromethane; water; ethyl acetate; acetone; tert-butyl alcohol;
DOI:10.1016/j.bmc.2005.09.044

Reference yield:

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

: 352219-99-9
(1S)-2-acetyl-1,5-dideoxy-1-C-heptadecyl-3,4-O-isopropylidene-6-O-tert-butyldiphenysilyl-1,5-imino-D-galactitol

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / DMAP / ethyl acetate / 0.08 h / 20 °C

2: 82 percent / PCC; florisil; sodium acetate / molecular sieves 4 Angstroem; Celite / CH₂Cl₂ / 3 h / 20 °C

3: 72 percent / sodium cyanoborohydride; ammonium formate; molecular sieves 4 Angstroem / methanol / 0.5 h / 20 °C

With dmap; florisil; 4 A molecular sieve; sodium acetate; ammonium formate; sodium cyanoborohydride; pyridinium chlorochromate; 4 A molecular sieve; Celite; In methanol; dichloromethane; ethyl acetate;
DOI:10.1016/j.bmc.2005.09.044