(3,4-di-O-benzyl-2-O-p-methoxybenzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-L-rhamnopyranosyl trichloroimidate

Base Information

Chemical Name:(3,4-di-O-benzyl-2-O-p-methoxybenzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-L-rhamnopyranosyl trichloroimidate
CAS No.:672907-61-8
Molecular Formula:C₅₀H₅₄Cl₃NO₁₀
Molecular Weight:935.338
Hs Code.:

Synonyms:(3,4-di-O-benzyl-2-O-p-methoxybenzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-L-rhamnopyranosyl trichloroimidate

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Chemical Property of (3,4-di-O-benzyl-2-O-p-methoxybenzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-L-rhamnopyranosyl trichloroimidate

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Technology Process of (3,4-di-O-benzyl-2-O-p-methoxybenzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-L-rhamnopyranosyl trichloroimidate

There total 6 articles about (3,4-di-O-benzyl-2-O-p-methoxybenzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-L-rhamnopyranosyl trichloroimidate 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: 82.0%

: 545-06-2
trichloroacetonitrile

: (3,4-di-O-benzyl-2-O-p-methoxybenzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-L-rhamnopyranose

: 672907-61-8
(3,4-di-O-benzyl-2-O-p-methoxybenzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-L-rhamnopyranosyl trichloroimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/jo035125b

Reference yield:

: 120022-54-0
allyl (3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

: 672907-61-8
(3,4-di-O-benzyl-2-O-p-methoxybenzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-L-rhamnopyranosyl trichloroimidate

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide

1.2: 97 percent / dimethylformamide / 20 °C

2.1: [Ir(COD){PCH₃(C₆H₅)2}2]PF₆ / tetrahydrofuran / 20 h / 20 °C

2.2: 73 percent / H₂O; HgO; HgCl₂ / acetone / 2 h / 20 °C

3.1: 82 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

With (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo035125b

Reference yield:

: 119471-45-3
allyl 3,4-di-O-benzyl-α-L-rhamnosylpyranose

: 672907-61-8
(3,4-di-O-benzyl-2-O-p-methoxybenzyl-α-L-rhamnopyranosyl)-(1->2)-3,4-di-O-benzyl-L-rhamnopyranosyl trichloroimidate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 92 percent / TMSOTf / diethyl ether / 3 h / -55 - -20 °C

2.1: 93 percent / NaOMe / methanol / 3 h / 20 °C

3.1: NaH / dimethylformamide

3.2: 97 percent / dimethylformamide / 20 °C

4.1: [Ir(COD){PCH₃(C₆H₅)2}2]PF₆ / tetrahydrofuran / 20 h / 20 °C

4.2: 73 percent / H₂O; HgO; HgCl₂ / acetone / 2 h / 20 °C

5.1: 82 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

With (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo035125b