(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1-3)-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-4)]-2-O-benzoyl-L-rhamnopyranosyl trichloroacetimidate

Base Information

Chemical Name:(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1-3)-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-4)]-2-O-benzoyl-L-rhamnopyranosyl trichloroacetimidate
CAS No.:502698-49-9
Molecular Formula:C₇₁H₇₄Cl₃NO₁₆
Molecular Weight:1303.72
Hs Code.:

(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1-3)-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-4)]-2-O-benzoyl-L-rhamnopyranosyl trichloroacetimidate

Synonyms:(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1-3)-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-4)]-2-O-benzoyl-L-rhamnopyranosyl trichloroacetimidate

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Chemical Property of (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1-3)-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-4)]-2-O-benzoyl-L-rhamnopyranosyl trichloroacetimidate

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Technology Process of (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1-3)-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-4)]-2-O-benzoyl-L-rhamnopyranosyl trichloroacetimidate

There total 7 articles about (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1-3)-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-4)]-2-O-benzoyl-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: 83.0%

: 545-06-2
trichloroacetonitrile

: (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1-3)-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-4)]-2-O-benzoyl-L-rhamnopyranose

: 502698-49-9
(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1-3)-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-4)]-2-O-benzoyl-L-rhamnopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1016/S0957-4166(02)00580-3

Reference yield:

: 100639-25-6,71695-57-3
allyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

: 502698-49-9
(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1-3)-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-4)]-2-O-benzoyl-L-rhamnopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 73 percent / TMSOTf / diethyl ether; CH₂Cl₂ / 3 h / -78 - -55 °C

2.1: 80 percent aq. AcOH / 4.5 h / 70 °C

3.1: CSA / CH₂Cl₂ / 2 h / 20 °C

3.2: 87 percent / 50 percent aq. TFA / CH₂Cl₂ / 0.83 h / 0 °C

4.1: 97 percent / TMSOTf / diethyl ether / 3 h / -78 - -30 °C

5.1: 75 percent / NaOAc / PdCl₂ / H₂O; acetic acid / 20 °C

6.1: 83 percent / DBU / CH₂Cl₂ / 4 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dichloride; In diethyl ether; dichloromethane; water; acetic acid;
DOI:10.1016/S0957-4166(02)00580-3

Reference yield:

: 90357-89-4
2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate

: 502698-49-9
(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1-3)-[(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1-4)]-2-O-benzoyl-L-rhamnopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 73 percent / TMSOTf / diethyl ether; CH₂Cl₂ / 3 h / -78 - -55 °C

2.1: 80 percent aq. AcOH / 4.5 h / 70 °C

3.1: CSA / CH₂Cl₂ / 2 h / 20 °C

3.2: 87 percent / 50 percent aq. TFA / CH₂Cl₂ / 0.83 h / 0 °C

4.1: 97 percent / TMSOTf / diethyl ether / 3 h / -78 - -30 °C

5.1: 75 percent / NaOAc / PdCl₂ / H₂O; acetic acid / 20 °C

6.1: 83 percent / DBU / CH₂Cl₂ / 4 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dichloride; In diethyl ether; dichloromethane; water; acetic acid;
DOI:10.1016/S0957-4166(02)00580-3