2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl trichloroacetimidate

Base Information

Chemical Name:2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl trichloroacetimidate
CAS No.:204199-49-5
Molecular Formula:C₂₄H₂₃Cl₄NO₇
Molecular Weight:579.261
Hs Code.:

Synonyms:2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl trichloroacetimidate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl trichloroacetimidate

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Technology Process of 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl trichloroacetimidate

There total 7 articles about 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl 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: 98.0%

: 545-06-2
trichloroacetonitrile

: 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α,β-L-rhamnopyranose

: 204199-49-5
2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/jo980660a

Reference yield:

: 100-39-0
benzyl bromide

: 204199-49-5
2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 2 h / 0 °C

2.1: 63.5 g / aq. AcOH / 3 h / 90 °C

3.1: 10-camphorsulfonic acid / CH₂Cl₂ / 1 h / 23 °C

3.2: 92 percent / aq. AcOH / 0.17 h

4.1: 77 percent / pyridine / 0.25 h / 0 °C

5.1: 87 percent / (CF₃CO₂)2Hg / CH₂Cl₂; H₂O / 2 h / 0 °C

6.1: 98 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

With pyridine; (1S)-10-camphorsulfonic acid; mercury(II) trifluoroacetate; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; water; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Hydrolysis / 3.1: Esterification / 3.2: Hydrolysis / 4.1: Acylation / 5.1: Hydrolysis / 6.1: Addition;
DOI:10.1021/jo980660a

Reference yield:

: 131087-35-9
phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

: 204199-49-5
2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 2 h / 0 °C

2.1: 63.5 g / aq. AcOH / 3 h / 90 °C

3.1: 10-camphorsulfonic acid / CH₂Cl₂ / 1 h / 23 °C

3.2: 92 percent / aq. AcOH / 0.17 h

4.1: 77 percent / pyridine / 0.25 h / 0 °C

5.1: 87 percent / (CF₃CO₂)2Hg / CH₂Cl₂; H₂O / 2 h / 0 °C

6.1: 98 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

With pyridine; (1S)-10-camphorsulfonic acid; mercury(II) trifluoroacetate; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; water; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Hydrolysis / 3.1: Esterification / 3.2: Hydrolysis / 4.1: Acylation / 5.1: Hydrolysis / 6.1: Addition;
DOI:10.1021/jo980660a