tert-butyldimethylsilyl methyl [methyl (2-O-acetyl-4-O-allyl-3-O-benzyl-α-L-idopyranosid)uronate-(1->4)-2-N-acetylacetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside-(1->4)-2-O-acetyl-3-O-benzyl-β-L-idopyranosid]uronate

Base Information

Chemical Name:tert-butyldimethylsilyl methyl [methyl (2-O-acetyl-4-O-allyl-3-O-benzyl-α-L-idopyranosid)uronate-(1->4)-2-N-acetylacetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside-(1->4)-2-O-acetyl-3-O-benzyl-β-L-idopyranosid]uronate
CAS No.:717902-51-7
Molecular Formula:C₆₅H₈₃NO₂₁Si
Molecular Weight:1242.45
Hs Code.:

tert-butyldimethylsilyl methyl [methyl (2-O-acetyl-4-O-allyl-3-O-benzyl-α-L-idopyranosid)uronate-(1->4)-2-N-acetylacetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside-(1->4)-2-O-acetyl-3-O-benzyl-β-L-idopyranosid]uronate

Synonyms:tert-butyldimethylsilyl methyl [methyl (2-O-acetyl-4-O-allyl-3-O-benzyl-α-L-idopyranosid)uronate-(1->4)-2-N-acetylacetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside-(1->4)-2-O-acetyl-3-O-benzyl-β-L-idopyranosid]uronate

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Chemical Property of tert-butyldimethylsilyl methyl [methyl (2-O-acetyl-4-O-allyl-3-O-benzyl-α-L-idopyranosid)uronate-(1->4)-2-N-acetylacetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside-(1->4)-2-O-acetyl-3-O-benzyl-β-L-idopyranosid]uronate

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Technology Process of tert-butyldimethylsilyl methyl [methyl (2-O-acetyl-4-O-allyl-3-O-benzyl-α-L-idopyranosid)uronate-(1->4)-2-N-acetylacetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside-(1->4)-2-O-acetyl-3-O-benzyl-β-L-idopyranosid]uronate

There total 9 articles about tert-butyldimethylsilyl methyl [methyl (2-O-acetyl-4-O-allyl-3-O-benzyl-α-L-idopyranosid)uronate-(1->4)-2-N-acetylacetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside-(1->4)-2-O-acetyl-3-O-benzyl-β-L-idopyranosid]uronate 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: 86.0%

: 108-22-5
Isopropenyl acetate

: 717902-50-6
tert-butyldimethylsilyl methyl [methyl (2-O-acetyl-4-O-allyl-3-O-benzyl-α-L-idopyranosid)uronate-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside-(1->4)-3-O-benzyl-β-L-idopyranosid]uronate

: 717902-51-7
tert-butyldimethylsilyl methyl [methyl (2-O-acetyl-4-O-allyl-3-O-benzyl-α-L-idopyranosid)uronate-(1->4)-2-N-acetylacetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside-(1->4)-2-O-acetyl-3-O-benzyl-β-L-idopyranosid]uronate

Guidance literature:: With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 90 ℃; for 5h; microwave irradiation;
DOI:10.1021/jo035732z

Reference yield:

: 120312-09-6
tert-Butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid

: 717902-51-7
tert-butyldimethylsilyl methyl [methyl (2-O-acetyl-4-O-allyl-3-O-benzyl-α-L-idopyranosid)uronate-(1->4)-2-N-acetylacetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside-(1->4)-2-O-acetyl-3-O-benzyl-β-L-idopyranosid]uronate

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -15 - 20 °C

2: tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran / 0.75 h / 0 °C

3: 950 mg / DBU / CH₂Cl₂ / 0 - 20 °C

4: 83 percent / trimethylsilyl trifluoromethanesulfonate; molecular sieves 4 Angstroem / CH₂Cl₂ / -25 °C

5: 84 percent / pyridine / 12 h

6: trifluoroacetic acid / 0.33 h

7: imidazole / CH₂Cl₂ / 16 h / -5 °C

8: 86 percent / p-toluenesulfonic acid / dimethylformamide / 5 h / 90 °C / microwave irradiation

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo035732z

Reference yield:

: 615543-04-9
methyl 2-O-acetyl-4-O-allyl-3-O-benzyl-L-idopyranosiduronate trichloroacetimidate

: 717902-51-7
tert-butyldimethylsilyl methyl [methyl (2-O-acetyl-4-O-allyl-3-O-benzyl-α-L-idopyranosid)uronate-(1->4)-2-N-acetylacetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside-(1->4)-2-O-acetyl-3-O-benzyl-β-L-idopyranosid]uronate

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -15 - 20 °C

2: tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran / 0.75 h / 0 °C

3: 950 mg / DBU / CH₂Cl₂ / 0 - 20 °C

4: 83 percent / trimethylsilyl trifluoromethanesulfonate; molecular sieves 4 Angstroem / CH₂Cl₂ / -25 °C

5: 84 percent / pyridine / 12 h

6: trifluoroacetic acid / 0.33 h

7: imidazole / CH₂Cl₂ / 16 h / -5 °C

8: 86 percent / p-toluenesulfonic acid / dimethylformamide / 5 h / 90 °C / microwave irradiation

With pyridine; 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo035732z