(3E,7E,12E)-(1R,15R,16S,17S,18S,20R,21S)-18-Benzyloxy-21-methoxymethoxy-4,8,12,17-tetramethyl-11-oxo-19-oxa-tricyclo[13.6.0.0^16,20]henicosa-3,7,12-triene-1-carboxylic acid methyl ester

Base Information

• Chemical Name: (3E,7E,12E)-(1R,15R,16S,17S,18S,20R,21S)-18-Benzyloxy-21-methoxymethoxy-4,8,12,17-tetramethyl-11-oxo-19-oxa-tricyclo[13.6.0.0^16,20]henicosa-3,7,12-triene-1-carboxylic acid methyl ester
• CAS No.: 211695-00-0
• Molecular Formula: C₃₅H₄₈O₇
• Molecular Weight: 580.762

Synonyms:(3E,7E,12E)-(1R,15R,16S,17S,18S,20R,21S)-18-Benzyloxy-21-methoxymethoxy-4,8,12,17-tetramethyl-11-oxo-19-oxa-tricyclo[13.6.0.0^16,20]henicosa-3,7,12-triene-1-carboxylic acid methyl ester

Chemical Property of (3E,7E,12E)-(1R,15R,16S,17S,18S,20R,21S)-18-Benzyloxy-21-methoxymethoxy-4,8,12,17-tetramethyl-11-oxo-19-oxa-tricyclo[13.6.0.0^16,20]henicosa-3,7,12-triene-1-carboxylic acid methyl ester

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Technology Process of (3E,7E,12E)-(1R,15R,16S,17S,18S,20R,21S)-18-Benzyloxy-21-methoxymethoxy-4,8,12,17-tetramethyl-11-oxo-19-oxa-tricyclo[13.6.0.0^16,20]henicosa-3,7,12-triene-1-carboxylic acid methyl ester

There total 9 articles about (3E,7E,12E)-(1R,15R,16S,17S,18S,20R,21S)-18-Benzyloxy-21-methoxymethoxy-4,8,12,17-tetramethyl-11-oxo-19-oxa-tricyclo[13.6.0.0^16,20]henicosa-3,7,12-triene-1-carboxylic acid methyl 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: 75.0%

(2R,3R,3aR,4S,5S,6R,6aS)-5-[(2E,6E)-10-Acetoxy-11-(diethoxy-phosphoryl)-3,7-dimethyl-dodeca-2,6-dienyl]-2-benzyloxy-6-methoxymethoxy-3-methyl-4-(2-oxo-ethyl)-hexahydro-cyclopenta[b]furan-5-carboxylic acid methyl ester → (3E,7E,12E)-(1R,15R,16S,17S,18S,20R,21S)-18-Benzyloxy-21-methoxymethoxy-4,8,12,17-tetramethyl-11-oxo-19-oxa-tricyclo[13.6.0.016,20]henicosa-3,7,12-triene-1-carboxylic acid methyl ester (211695-00-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; at 20 ℃; for 72h;

DOI:10.7164/antibiotics.51.602

Reference yield:

(2S,3S,3aS,3bR,8aR)-2-Benzyloxy-3-methyl-octahydro-furo[3',2':3,4]cyclopenta[1,2-c]pyran-7,8-dione → (3E,7E,12E)-(1R,15R,16S,17S,18S,20R,21S)-18-Benzyloxy-21-methoxymethoxy-4,8,12,17-tetramethyl-11-oxo-19-oxa-tricyclo[13.6.0.016,20]henicosa-3,7,12-triene-1-carboxylic acid methyl ester (211695-00-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / Cs₂CO₃; CsI / acetonitrile / 3 h / 50 °C

2: NaBH₄ / methanol / 0.25 h / 0 °C

3: 92 percent / DIPEA / 1,2-dichloro-ethane / 1 h / 60 °C

4: LiOH / H₂O; methanol / 1 h / 60 °C

5: 80 percent / hexamethylphosphoric acid triamide / 0.5 h / 20 °C

6: 78 percent / TPAP; NMO / CH₂Cl₂ / 3 h / 20 °C

7: 75 percent / DIPEA; LiCl / acetonitrile / 72 h / 20 °C

With lithium hydroxide; sodium tetrahydroborate; isocyanate de chlorosulfonyle; N-methyl-2-indolinone; tetrapropylammonium perruthennate; caesium carbonate; N-ethyl-N,N-diisopropylamine; lithium chloride; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; 1: Alkylation / 2: Reduction / 3: Alkylation / 4: Ring cleavage / 5: Esterification / 6: Oxidation / 7: Cyclization;

DOI:10.7164/antibiotics.51.602

Reference yield:

Acetic acid (4E,8E)-10-((2R,3R,3aR,3bS,7aS,8R,8aS)-2-benzyloxy-8-hydroxy-3-methyl-7-oxo-octahydro-furo[3',2':3,4]cyclopenta[1,2-c]pyran-7a-yl)-1-[1-(diethoxy-phosphoryl)-ethyl]-4,8-dimethyl-deca-4,8-dienyl ester → (3E,7E,12E)-(1R,15R,16S,17S,18S,20R,21S)-18-Benzyloxy-21-methoxymethoxy-4,8,12,17-tetramethyl-11-oxo-19-oxa-tricyclo[13.6.0.016,20]henicosa-3,7,12-triene-1-carboxylic acid methyl ester (211695-00-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / DIPEA / 1,2-dichloro-ethane / 1 h / 60 °C

2: LiOH / H₂O; methanol / 1 h / 60 °C

3: 80 percent / hexamethylphosphoric acid triamide / 0.5 h / 20 °C

4: 78 percent / TPAP; NMO / CH₂Cl₂ / 3 h / 20 °C

5: 75 percent / DIPEA; LiCl / acetonitrile / 72 h / 20 °C

With lithium hydroxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; N-ethyl-N,N-diisopropylamine; lithium chloride; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; 1: Alkylation / 2: Ring cleavage / 3: Esterification / 4: Oxidation / 5: Cyclization;

DOI:10.7164/antibiotics.51.602

upstream raw materials:

Acetic acid (4E,8E)-10-chloro-1-[1-(diethoxy-phosphoryl)-ethyl]-4,8-dimethyl-deca-4,8-dienyl ester

Downstream raw materials:

[(3E,7E,12E)-(1S,11R,15R,16S,17S,18S,20R,21S)-18-Benzyloxy-11-(tert-butyl-dimethyl-silanyloxy)-21-methoxymethoxy-4,8,12,17-tetramethyl-19-oxa-tricyclo[13.6.0.0^16,20]henicosa-3,7,12-trien-1-yl]-methanol

C₃₉H₅₀O₆

(3E,7E,12E)-(1S,11S,15R,16S,17S,18S,20R,21S)-18-Benzyloxy-21-methoxymethoxy-1,4,8,12,17-pentamethyl-19-oxa-tricyclo[13.6.0.0^16,20]henicosa-3,7,12-trien-11-ol

(3E,7E,12E)-(1S,15R,16S,17S,18S,20R,21S)-18-Benzyloxy-21-methoxymethoxy-1,4,8,12,17-pentamethyl-19-oxa-tricyclo[13.6.0.0^16,20]henicosa-3,7,12-trien-11-one

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