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-1,2-isopropylidene-β-L-idopyranosid]uronate

Base Information

Chemical Name: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-1,2-isopropylidene-β-L-idopyranosid]uronate
CAS No.:717902-49-3
Molecular Formula:C₅₈H₆₉NO₁₉
Molecular Weight:1084.18
Hs Code.:

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-1,2-isopropylidene-β-L-idopyranosid]uronate

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Chemical Property of 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-1,2-isopropylidene-β-L-idopyranosid]uronate

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Technology Process of 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-1,2-isopropylidene-β-L-idopyranosid]uronate

There total 6 articles about 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-1,2-isopropylidene-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: 84.0%

: 507-09-5
tiolacetic acid

: 717902-48-2
methyl [methyl (2-O-acetyl-4-O-allyl-3-O-benzyl-α-L-idopyranosid)uronate-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside-(1->4)-3-O-benzyl-1,2-isopropylidene-β-L-idopyranosid]uronate

: 717902-49-3
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-1,2-isopropylidene-β-L-idopyranosid]uronate

Guidance literature:: With pyridine; for 12h;
DOI:10.1021/jo035732z

Reference yield:

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

: 717902-49-3
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-1,2-isopropylidene-β-L-idopyranosid]uronate

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

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

: 717902-49-3
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-1,2-isopropylidene-β-L-idopyranosid]uronate

Guidance literature:: Multi-step reaction with 5 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

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