methyl (E,2S,3R,4R)-4-benzyloxy-3,8-dihydroxy-2-(4-methoxybenzyloxymethyl)-2-(trichloroacetamido)oct-6-enoate

Base Information

Chemical Name:methyl (E,2S,3R,4R)-4-benzyloxy-3,8-dihydroxy-2-(4-methoxybenzyloxymethyl)-2-(trichloroacetamido)oct-6-enoate
CAS No.:386765-90-8
Molecular Formula:C₂₇H₃₂Cl₃NO₈
Molecular Weight:604.912
Hs Code.:

Synonyms:methyl (E,2S,3R,4R)-4-benzyloxy-3,8-dihydroxy-2-(4-methoxybenzyloxymethyl)-2-(trichloroacetamido)oct-6-enoate

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Chemical Property of methyl (E,2S,3R,4R)-4-benzyloxy-3,8-dihydroxy-2-(4-methoxybenzyloxymethyl)-2-(trichloroacetamido)oct-6-enoate

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Technology Process of methyl (E,2S,3R,4R)-4-benzyloxy-3,8-dihydroxy-2-(4-methoxybenzyloxymethyl)-2-(trichloroacetamido)oct-6-enoate

There total 20 articles about methyl (E,2S,3R,4R)-4-benzyloxy-3,8-dihydroxy-2-(4-methoxybenzyloxymethyl)-2-(trichloroacetamido)oct-6-enoate 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%

: 386765-89-5
1-ethyl 8-methyl (E,5R,6R,7S)-5-benzyloxy-6-hydroxy-7-(4-methoxybenzyloxymethyl)-7-(trichloroacetamido)oct-2-enedioate

: 386765-90-8
methyl (E,2S,3R,4R)-4-benzyloxy-3,8-dihydroxy-2-(4-methoxybenzyloxymethyl)-2-(trichloroacetamido)oct-6-enoate

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -18 ℃; for 0.25h;
DOI:10.1246/bcsj.75.1927

Reference yield:

: 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

: 386765-90-8
methyl (E,2S,3R,4R)-4-benzyloxy-3,8-dihydroxy-2-(4-methoxybenzyloxymethyl)-2-(trichloroacetamido)oct-6-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: K₂CO₃ / xylene / 60 h / 140 °C

1.2: ozone / methanol / 0.25 h / -78 °C

1.3: 486 mg / Me₂S / methanol / -78 - 0 °C

2.1: NaH₂PO₄*2H₂O; HOSO₂NH₂; NaClO₂ / H₂O; 2-methyl-propan-2-ol / 0.25 h / 25 °C

3.1: 405 mg / methanol / 1 h / 25 °C

4.1: 76 percent / aqueous HCl / tetrahydrofuran / 10 h / 25 °C

5.1: 89 percent / toluene / 20 h / 25 °C

6.1: 82 percent / DIBAL-H / tetrahydrofuran; toluene / 0.25 h / -18 °C

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; amidosulfuric acid fluoride; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol; water; toluene; xylene; tert-butyl alcohol; 1.1: Overman rearrangement;
DOI:10.1246/bcsj.75.1927

Reference yield:

: 386765-87-3
methyl (S)-2-[(2R,3R,5S)-3-benzyloxy-5-methoxyoxolan-2-yl]-3-(4-methoxybenzyloxy)-2-(trichloroacetamido)propanoate

: 386765-90-8
methyl (E,2S,3R,4R)-4-benzyloxy-3,8-dihydroxy-2-(4-methoxybenzyloxymethyl)-2-(trichloroacetamido)oct-6-enoate

Guidance literature:: Multi-step reaction with 3 steps

1: 76 percent / aqueous HCl / tetrahydrofuran / 10 h / 25 °C

2: 89 percent / toluene / 20 h / 25 °C

3: 82 percent / DIBAL-H / tetrahydrofuran; toluene / 0.25 h / -18 °C

With hydrogenchloride; diisobutylaluminium hydride; In tetrahydrofuran; toluene;
DOI:10.1246/bcsj.75.1927