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-β-D-glucopyranoside trichloroacetimidate

Base Information

Chemical Name: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-β-D-glucopyranoside trichloroacetimidate
CAS No.:717902-47-1
Molecular Formula:C₄₁H₄₅Cl₃N₄O₁₂
Molecular Weight:892.187
Hs Code.:

Synonyms: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-β-D-glucopyranoside trichloroacetimidate

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Chemical Property of 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-β-D-glucopyranoside trichloroacetimidate

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Technology Process of 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-β-D-glucopyranoside trichloroacetimidate

There total 4 articles about 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-β-D-glucopyranoside trichloroacetimidate 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:

: 545-06-2
trichloroacetonitrile

: (2R,3S,4S,5R,6R)-5-Acetoxy-3-allyloxy-6-((2R,3S,4R,5R)-5-azido-4-benzyloxy-2-benzyloxymethyl-6-hydroxy-tetrahydro-pyran-3-yloxy)-4-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 717902-47-1
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-β-D-glucopyranoside trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/jo035732z

Reference yield:

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

: 717902-47-1
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-β-D-glucopyranoside trichloroacetimidate

Guidance literature:: Multi-step reaction with 3 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

With trimethylsilyl trifluoromethanesulfonate; 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

: 717902-47-1
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-β-D-glucopyranoside trichloroacetimidate

Guidance literature:: Multi-step reaction with 3 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

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