2,2,2-Trichloro-acetimidic acid (E)-3-((2R,3R,5S)-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-4-(4-methoxy-benzyloxy)-but-2-enyl ester

Base Information

Chemical Name:2,2,2-Trichloro-acetimidic acid (E)-3-((2R,3R,5S)-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-4-(4-methoxy-benzyloxy)-but-2-enyl ester
CAS No.:386765-82-8
Molecular Formula:C₂₆H₃₀Cl₃NO₆
Molecular Weight:558.886
Hs Code.:

Synonyms:2,2,2-Trichloro-acetimidic acid (E)-3-((2R,3R,5S)-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-4-(4-methoxy-benzyloxy)-but-2-enyl ester

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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 2,2,2-Trichloro-acetimidic acid (E)-3-((2R,3R,5S)-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-4-(4-methoxy-benzyloxy)-but-2-enyl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 2,2,2-Trichloro-acetimidic acid (E)-3-((2R,3R,5S)-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-4-(4-methoxy-benzyloxy)-but-2-enyl ester

There total 12 articles about 2,2,2-Trichloro-acetimidic acid (E)-3-((2R,3R,5S)-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-4-(4-methoxy-benzyloxy)-but-2-enyl ester 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

: 184964-62-3
(E)-3-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-4-(4-methoxybenzyloxy)but-2-en-1-ol

: 386765-82-8
2,2,2-Trichloro-acetimidic acid (E)-3-((2R,3R,5S)-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-4-(4-methoxy-benzyloxy)-but-2-enyl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1246/bcsj.75.1927

Reference yield:

: 386765-73-7
methyl 3-O-benzyl-2-deoxy-α-D-arabino-hexofuranoside

: 386765-82-8
2,2,2-Trichloro-acetimidic acid (E)-3-((2R,3R,5S)-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-4-(4-methoxy-benzyloxy)-but-2-enyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: dibutyltin oxide / toluene / 2 h / Heating

1.2: 96 percent / CsF / dimethylformamide / 40 h / 80 °C

2.1: 100 percent / (COCl)2; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 3.5 h / -78 - 0 °C

3.1: 90 percent / LiBr; DBU / acetonitrile / 12 h / -45 °C

4.1: 93 percent / DIBAL-H; DBU / toluene / 0.25 h / -78 °C

5.1: DBU / CH₂Cl₂ / 0.5 h / 0 °C

With oxalyl dichloride; diisobutylaluminium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium bromide; In dichloromethane; toluene; acetonitrile; 2.1: Swern oxidation;
DOI:10.1246/bcsj.75.1927

Reference yield:

: 386765-77-1
methyl 3-O-benzyl-6-O-(4-methoxybenzyl)-2-deoxy-α-D-threo-hexofuranos-5-uloside

: 386765-82-8
2,2,2-Trichloro-acetimidic acid (E)-3-((2R,3R,5S)-3-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-4-(4-methoxy-benzyloxy)-but-2-enyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / LiBr; DBU / acetonitrile / 12 h / -45 °C

2: 93 percent / DIBAL-H; DBU / toluene / 0.25 h / -78 °C

3: DBU / CH₂Cl₂ / 0.5 h / 0 °C

With diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium bromide; In dichloromethane; toluene; acetonitrile;
DOI:10.1246/bcsj.75.1927