methyl 2-O-acetyl-4-O-allyl-3-O-benzyl-L-idopyranosiduronate trichloroacetimidate

Base Information

• Chemical Name: methyl 2-O-acetyl-4-O-allyl-3-O-benzyl-L-idopyranosiduronate trichloroacetimidate
• CAS No.: 615543-04-9
• Molecular Formula: C₂₁H₂₄Cl₃NO₈
• Molecular Weight: 524.782

Synonyms:methyl 2-O-acetyl-4-O-allyl-3-O-benzyl-L-idopyranosiduronate trichloroacetimidate

Chemical Property of methyl 2-O-acetyl-4-O-allyl-3-O-benzyl-L-idopyranosiduronate trichloroacetimidate

Chemical Property:

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Technology Process of methyl 2-O-acetyl-4-O-allyl-3-O-benzyl-L-idopyranosiduronate trichloroacetimidate

There total 14 articles about methyl 2-O-acetyl-4-O-allyl-3-O-benzyl-L-idopyranosiduronate 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: 92.0%

trichloroacetonitrile (545-06-2) + (2R,3S,4S,5R)-5-Acetoxy-3-allyloxy-4-benzyloxy-6-hydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester → methyl 2-O-acetyl-4-O-allyl-3-O-benzyl-L-idopyranosiduronate trichloroacetimidate (615543-04-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1021/jo0340760

Reference yield:

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol (22529-61-9) → methyl 2-O-acetyl-4-O-allyl-3-O-benzyl-L-idopyranosiduronate trichloroacetimidate (615543-04-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium periodate; silica gel / CH₂Cl₂; H₂O / 1.5 h

2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - -50 °C

2.2: tetrahydrofuran; hexane / 1.5 h / -78 - 20 °C

3.1: CuCl₂; CuO / H₂O; CH₂Cl₂ / 0.08 h / 20 °C

3.2: 437 mg / K₂CO₃ / CH₂Cl₂; methanol / 1.5 h / 20 °C

4.1: trifluoroacetic acid / H₂O / 0.58 h / 20 °C

5.1: (+)-camphorsulfonic acid / dimethylformamide / 3 h / 0 °C

5.2: 199 mg / Dowex 50W acidic resin / methanol / 0.33 h / 20 °C

6.1: 70 percent / molecular sieves 4 Angstroem; Ag₂O / CH₂Cl₂ / 72 h

7.1: trifluoroacetic acid / H₂O / 0.5 h

8.1: pyridine; DMAP / CH₂Cl₂

9.1: 85 percent / benzylamine / tetrahydrofuran / 5.5 h

10.1: 92 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; dmap; sodium periodate; n-butyllithium; 4 A molecular sieve; silica gel; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-10-camphorsulfonic acid; benzylamine; trifluoroacetic acid; copper(II) oxide; copper dichloride; silver(l) oxide; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo0340760

Reference yield:

benzyl bromide (100-39-0) → methyl 2-O-acetyl-4-O-allyl-3-O-benzyl-L-idopyranosiduronate trichloroacetimidate (615543-04-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: NaH; tetrabutylammonium iodide / tetrahydrofuran / 14 h / 20 °C

2.1: 17.8 g / acetic acid / H₂O / 16 h / 20 °C

3.1: sodium periodate; silica gel / CH₂Cl₂; H₂O / 1.5 h

4.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - -50 °C

4.2: tetrahydrofuran; hexane / 1.5 h / -78 - 20 °C

5.1: CuCl₂; CuO / H₂O; CH₂Cl₂ / 0.08 h / 20 °C

5.2: 437 mg / K₂CO₃ / CH₂Cl₂; methanol / 1.5 h / 20 °C

6.1: trifluoroacetic acid / H₂O / 0.58 h / 20 °C

7.1: (+)-camphorsulfonic acid / dimethylformamide / 3 h / 0 °C

7.2: 199 mg / Dowex 50W acidic resin / methanol / 0.33 h / 20 °C

8.1: 70 percent / molecular sieves 4 Angstroem; Ag₂O / CH₂Cl₂ / 72 h

9.1: trifluoroacetic acid / H₂O / 0.5 h

10.1: pyridine; DMAP / CH₂Cl₂

11.1: 85 percent / benzylamine / tetrahydrofuran / 5.5 h

12.1: 92 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

With pyridine; dmap; sodium periodate; n-butyllithium; 4 A molecular sieve; silica gel; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-10-camphorsulfonic acid; benzylamine; trifluoroacetic acid; copper(II) oxide; copper dichloride; silver(l) oxide; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo0340760

upstream raw materials:

trichloroacetonitrile

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

benzyl bromide

3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

Downstream raw materials:

tert-butyldimethylsilyl (methyl 2-O-acetyl-4-O-allyl-3-O-benzyl-α-L-idopyranosiduronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

methyl methyl 2-O-acetyl-4-O-allyl-3-O-benzyl-α-L-idopyrnosiduronate-(1->4)-3,6-di-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside

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 trichloroacetimidate

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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