N-[(R)-1-benzyloxy-2-{(1R,5R,7R,8S)-3,3-dimethyl-8-methoxymethoxy-2,4,6-trioxabicyclo[3.3.0]octane-7-yl}but-3-en-2-yl]trichloroacetamide

Base Information

• Chemical Name: N-[(R)-1-benzyloxy-2-{(1R,5R,7R,8S)-3,3-dimethyl-8-methoxymethoxy-2,4,6-trioxabicyclo[3.3.0]octane-7-yl}but-3-en-2-yl]trichloroacetamide
• CAS No.: 184964-57-6
• Molecular Formula: C₂₂H₂₈Cl₃NO₇
• Molecular Weight: 524.826

Synonyms:N-[(R)-1-benzyloxy-2-{(1R,5R,7R,8S)-3,3-dimethyl-8-methoxymethoxy-2,4,6-trioxabicyclo[3.3.0]octane-7-yl}but-3-en-2-yl]trichloroacetamide

Chemical Property of N-[(R)-1-benzyloxy-2-{(1R,5R,7R,8S)-3,3-dimethyl-8-methoxymethoxy-2,4,6-trioxabicyclo[3.3.0]octane-7-yl}but-3-en-2-yl]trichloroacetamide

Chemical Property:

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Technology Process of N-[(R)-1-benzyloxy-2-{(1R,5R,7R,8S)-3,3-dimethyl-8-methoxymethoxy-2,4,6-trioxabicyclo[3.3.0]octane-7-yl}but-3-en-2-yl]trichloroacetamide

There total 12 articles about N-[(R)-1-benzyloxy-2-{(1R,5R,7R,8S)-3,3-dimethyl-8-methoxymethoxy-2,4,6-trioxabicyclo[3.3.0]octane-7-yl}but-3-en-2-yl]trichloroacetamide 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: 60.0%

2,2,2-Trichloro-acetimidic acid (Z)-4-benzyloxy-3-((3aR,5R,6S,6aR)-6-methoxymethoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-2-enyl ester (397870-66-5) → N-[(S)-1-benzyloxy-2-{(1R,5R,7R,8S)-3,3-dimethyl-8-methoxymethoxy-2,4,6-trioxabicyclo[3.3.0]octane-7-yl}but-3-en-2-yl]trichloroacetamide + N-[(R)-1-benzyloxy-2-{(1R,5R,7R,8S)-3,3-dimethyl-8-methoxymethoxy-2,4,6-trioxabicyclo[3.3.0]octane-7-yl}but-3-en-2-yl]trichloroacetamide (184964-57-6)

Guidance literature:

With potassium carbonate; In xylene; at 140 ℃; for 140h;

DOI:10.1021/ol0171620

Reference yield: 11.0%

trichloroacetonitrile (545-06-2) + (E)-4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]oct-7-yl}but-2-en-1-ol (397870-78-9) → N-[(S)-1-benzyloxy-2-{(1R,5R,7R,8S)-3,3-dimethyl-8-methoxymethoxy-2,4,6-trioxabicyclo[3.3.0]octane-7-yl}but-3-en-2-yl]trichloroacetamide + N-[(R)-1-benzyloxy-2-{(1R,5R,7R,8S)-3,3-dimethyl-8-methoxymethoxy-2,4,6-trioxabicyclo[3.3.0]octane-7-yl}but-3-en-2-yl]trichloroacetamide (184964-57-6)

Guidance literature:

trichloroacetonitrile; (E)-4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]oct-7-yl}but-2-en-1-ol; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃;

With potassium carbonate; In xylene; at 140 ℃; Further stages.;

DOI:10.1021/ol0171620

Reference yield:

1,2-O-isopropylidene-3-O-methoxymethyl-α-D-glucofuranose (104487-62-9) → N-[(R)-1-benzyloxy-2-{(1R,5R,7R,8S)-3,3-dimethyl-8-methoxymethoxy-2,4,6-trioxabicyclo[3.3.0]octane-7-yl}but-3-en-2-yl]trichloroacetamide (184964-57-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dibutyltin oxide / toluene / 3 h / Heating

1.2: 88 percent / CsF / dimethylformamide / 13 h / 80 °C

2.1: 100 percent / (COCl)2; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 1.25 h / -78 - 0 °C

3.1: 98 percent / toluene / 17 h / 100 °C

4.1: 73 percent / DIBAL-H / toluene / 3 h / -78 °C

5.1: DBU / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 89.4 mg / K₂CO₃ / xylene / 156 h / 140 °C

With oxalyl dichloride; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; toluene; xylene; 2.1: Swern oxidation / 6.1: Overman rearrangement;

DOI:10.1246/bcsj.75.1927

upstream raw materials:

trichloroacetonitrile

(E)-4-benzyloxy-3-{(1R,5R,7R,8S)-8-methoxymethoxy-3,3-dimethyl-2,4,6-trioxabicyclo[3.3.0]oct-7-yl}but-2-en-1-ol

2,2,2-Trichloro-acetimidic acid (Z)-4-benzyloxy-3-((3aR,5R,6S,6aR)-6-methoxymethoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-but-2-enyl ester

benzyl bromide

Downstream raw materials:

((4R,5S)-4-{(4R,5S)-5-[(E)-4-Benzenesulfonyl-8-(2-hexyl-[1,3]dioxolan-2-yl)-oct-1-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-carbamic acid tert-butyl ester

(E)-(4S,5R,6R,7R)-8-Benzyloxy-4,5,6-trihydroxy-7-hydroxymethyl-7-(2,2,2-trichloro-acetylamino)-oct-2-enoic acid ethyl ester

N-[(R)-2-Benzyloxy-1-hydroxymethyl-1-((3aR,5R,6S,6aR)-6-methoxymethoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethyl]-2,2,2-trichloro-acetamide

Methanesulfonic acid (E)-3-[(4S,5R)-5-((4R,5S)-5-benzyloxymethyl-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-allyl ester

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