(1S)-1,5-anhydro-1-C-heptadecyl-3,4-O-isopropylidene-6-O-tert-butyldiphenysilyl-D-galactitol

Base Information

Chemical Name:(1S)-1,5-anhydro-1-C-heptadecyl-3,4-O-isopropylidene-6-O-tert-butyldiphenysilyl-D-galactitol
CAS No.:224325-00-2
Molecular Formula:C₄₂H₆₈O₅Si
Molecular Weight:681.084
Hs Code.:

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

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

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

There total 13 articles about (1S)-1,5-anhydro-1-C-heptadecyl-3,4-O-isopropylidene-6-O-tert-butyldiphenysilyl-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: 76.0%

: 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

: 224325-00-2
(1S)-1,5-anhydro-1-C-heptadecyl-3,4-O-isopropylidene-6-O-tert-butyldiphenysilyl-D-galactitol

Guidance literature:: tert-butyl-(6-heptadecyl-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy)-diphenyl-silane; With dimethylsulfide borane complex; In tetrahydrofuran; dichloromethane; at 20 ℃; for 1h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1016/j.bmc.2005.09.044

Reference yield:

: 4099-88-1,67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1
(3aR,4S,6R,6aS)-6-(hydroxymethyl)-2,2-dimethylperhydrocyclopenta[d][1,3]dioxol-4-ol

: 224325-00-2
(1S)-1,5-anhydro-1-C-heptadecyl-3,4-O-isopropylidene-6-O-tert-butyldiphenysilyl-D-galactitol

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent

2: 95 percent / I₂

3: 1.) BF₃*Et₂O, 2.) MeONa / 1.) CH₂Cl₂, -78 deg C

4: DCC, DMAP / benzene

6: 76 percent / MeOTf, 2,6-di-t-butyl-4-methylpyridine / CH₂Cl₂

7: 1.) BH₃*DMS, 2.) Na₂O₂

With dmap; 2,6-di-tert-butyl-4-methylpyridine; sodium peroxide; dimethylsulfide borane complex; boron trifluoride diethyl etherate; iodine; sodium methylate; dicyclohexyl-carbodiimide; methyl trifluoromethanesulfonate; In dichloromethane; benzene;
DOI:10.1021/ja9843270

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 224325-00-2
(1S)-1,5-anhydro-1-C-heptadecyl-3,4-O-isopropylidene-6-O-tert-butyldiphenysilyl-D-galactitol

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent

2: 95 percent / I₂

3: 1.) BF₃*Et₂O, 2.) MeONa / 1.) CH₂Cl₂, -78 deg C

4: DCC, DMAP / benzene

6: 76 percent / MeOTf, 2,6-di-t-butyl-4-methylpyridine / CH₂Cl₂

7: 1.) BH₃*DMS, 2.) Na₂O₂

With dmap; 2,6-di-tert-butyl-4-methylpyridine; sodium peroxide; dimethylsulfide borane complex; boron trifluoride diethyl etherate; iodine; sodium methylate; dicyclohexyl-carbodiimide; methyl trifluoromethanesulfonate; In dichloromethane; benzene;
DOI:10.1021/ja9843270