Acetic acid (2S,3R,4R,5S,6R)-2-acetoxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Acetic acid (2S,3R,4R,5S,6R)-2-acetoxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester
CAS No.:157567-46-9
Molecular Formula:C₃₁H₃₉NO₉Si
Molecular Weight:597.737
Hs Code.:

Acetic acid (2S,3R,4R,5S,6R)-2-acetoxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

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Chemical Property of Acetic acid (2S,3R,4R,5S,6R)-2-acetoxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2S,3R,4R,5S,6R)-2-acetoxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

There total 9 articles about Acetic acid (2S,3R,4R,5S,6R)-2-acetoxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester 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: 73.0%

: 108-24-7
acetic anhydride

: 157567-44-7
Acetic acid (2R,3S,4R,5R,6R)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxy-tetrahydro-pyran-4-yl ester

: 157567-46-9
Acetic acid (2S,3R,4R,5S,6R)-2-acetoxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Guidance literature:: With pyridine;

Reference yield:

: 10022-13-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

: 157567-46-9
Acetic acid (2S,3R,4R,5S,6R)-2-acetoxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 96 percent / HBr / acetic acid

2: 74 percent / Hg(CN)2

3: 53 percent / aq. HCl / acetone

4: 82 percent / TsOH

5: 91 percent / pyridine

6: 80 percent / NaBH₃CN, HCl

7: 77 percent / imidazole

8: 2.) OsO₄, Me₃NO / 1.) CODIr(PMePh₂)2⁽¹⁺⁾PF₆^(1-)

9: 73 percent / pyridine

With pyridine; 1H-imidazole; hydrogenchloride; osmium(VIII) oxide; trimethylamine-N-oxide; hydrogen bromide; mercury(II) cyanide; sodium cyanoborohydride; toluene-4-sulfonic acid; (bis(diphenylphosphino)ethylene)(1,5-cyclooctadiene)iridium(I) hexafluorophosphate; In acetic acid; acetone;

Reference yield:

: 72333-26-7
allyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

: 157567-46-9
Acetic acid (2S,3R,4R,5S,6R)-2-acetoxy-6-benzyloxymethyl-5-(tert-butyl-dimethyl-silanyloxy)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 53 percent / aq. HCl / acetone

2: 82 percent / TsOH

3: 91 percent / pyridine

4: 80 percent / NaBH₃CN, HCl

5: 77 percent / imidazole

6: 2.) OsO₄, Me₃NO / 1.) CODIr(PMePh₂)2⁽¹⁺⁾PF₆^(1-)

7: 73 percent / pyridine

With pyridine; 1H-imidazole; hydrogenchloride; osmium(VIII) oxide; trimethylamine-N-oxide; sodium cyanoborohydride; toluene-4-sulfonic acid; (bis(diphenylphosphino)ethylene)(1,5-cyclooctadiene)iridium(I) hexafluorophosphate; In acetone;