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

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 157567-45-8
• Molecular Formula: C₃₁H₃₇Cl₃N₂O₈Si
• Molecular Weight: 700.088
• Mol file: 157567-45-8.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about Acetic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2,2,2-trichloro-acetimidoyloxy)-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: 56.0%

trichloroacetonitrile (545-06-2) + 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 (157567-44-7) → Acetic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester (157567-45-8)

Guidance literature:

With sodium hydride;

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) → Acetic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester (157567-45-8)

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: 56 percent / NaH

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

Reference yield:

allyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside (72333-26-7) → Acetic acid (2R,3S,4R,5R,6S)-2-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester (157567-45-8)

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: 56 percent / NaH

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

upstream raw materials:

trichloroacetonitrile

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

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

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

Downstream raw materials:

C₅₅H₆₂N₂O₁₅Si

C₄₉H₄₈N₂O₁₅