(1S,4R,5R,7R,9R,13S,14S,15S)-3,11-dioxo-4-hydroxy-9-[(E)-2-iodoethenyl]-15-[[3-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]actadecane

Base Information

• Chemical Name: (1S,4R,5R,7R,9R,13S,14S,15S)-3,11-dioxo-4-hydroxy-9-[(E)-2-iodoethenyl]-15-[[3-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]actadecane
• CAS No.: 215120-40-4
• Molecular Formula: C₄₃H₆₃IO₁₅
• Molecular Weight: 946.869
• Mol file: 215120-40-4.mol

Synonyms:(1S,4R,5R,7R,9R,13S,14S,15S)-3,11-dioxo-4-hydroxy-9-[(E)-2-iodoethenyl]-15-[[3-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]actadecane

Chemical Property of (1S,4R,5R,7R,9R,13S,14S,15S)-3,11-dioxo-4-hydroxy-9-[(E)-2-iodoethenyl]-15-[[3-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]actadecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R,5R,7R,9R,13S,14S,15S)-3,11-dioxo-4-hydroxy-9-[(E)-2-iodoethenyl]-15-[[3-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]actadecane

There total 64 articles about (1S,4R,5R,7R,9R,13S,14S,15S)-3,11-dioxo-4-hydroxy-9-[(E)-2-iodoethenyl]-15-[[3-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]actadecane 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: 39.0%

3-[4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thiophenyl-β-D-xylopyranose (171613-34-6) + (1S,4R,5R,7R,9R,13S,14R,15S)-4,15-dihydroxy-3,11-dioxo-9-[(E)-2-iodoethenyl]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.14,7]octadecane (215120-26-6) → (1S,4R,5R,7R,9R,13S,14S,15S)-3,11-dioxo-4-hydroxy-9-[(E)-2-iodoethenyl]-15-[[3-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.14,7]actadecane (215120-40-4)

Guidance literature:

With N-Bromosuccinimide; In acetonitrile; at -35 - 20 ℃; for 4h; Inert atmosphere; Molecular sieve;

DOI:10.1021/ja1009579

Reference yield:

((2S,3R,4S,6S)-4-Benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-2-yl)-acetic acid methyl ester (162718-31-2) → (1S,4R,5R,7R,9R,13S,14S,15S)-3,11-dioxo-4-hydroxy-9-[(E)-2-iodoethenyl]-15-[[3-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.14,7]actadecane (215120-40-4)

Guidance literature:

Multi-step reaction with 20 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 20 min, 2.) CH₂Cl₂, from -78 deg C to 0 deg C

2: tetrahydrofuran / a) -78 deg C, 5 min, b) 20 deg C, 16 h

3: 92 percent / aq. TFA / tetrahydrofuran / 4.5 h / 20 °C

4: ZnI₂ / CH₂Cl₂ / 5.5 h / 20 °C

5: LiAlH₄ / tetrahydrofuran / 0 °C

6: imidazole / dimethylformamide / 0 °C

7: 93 percent / m-CPBA / CH₂Cl₂ / -60 °C

8: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 30 min

9: 65 percent / p-TsOH*H₂O, MeOH / 72 h / 25 °C

10: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 20 min, 2.) CH₂Cl₂, from -60 deg C to 0 deg C

11: 92 percent / DDQ / CH₂Cl₂ / 2.5 h / 20 °C

12: aq. NaClO₂, aq. NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.33 h / 0 °C

13: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 20 deg C, 10 h, 2.) toluene, 60 deg C, 1 h

14: OsO₄, NMO / dioxane; H₂O / 31 h / 20 °C

15: aq. NaIO₄ / dioxane / 0.67 h

16: H₂ / Pd/C / methanol / 0.67 h / 20 °C

17: 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

18: CrCl₂ / tetrahydrofuran / 0.5 h / 0 °C

19: aq. TFA / tetrahydrofuran / 6.5 h / 20 °C

20: NBS, 4A MS / acetonitrile / 0.08 h / -20 °C

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; methanol; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; N-Bromosuccinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 2-methyl-but-2-ene; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) iodide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja982431b

Reference yield:

[(2S,3R,4S,6S)-4-Benzyloxy-3-methyl-6-(2-oxo-ethyl)-tetrahydro-pyran-2-yl]-acetic acid methyl ester (215120-31-3) → (1S,4R,5R,7R,9R,13S,14S,15S)-3,11-dioxo-4-hydroxy-9-[(E)-2-iodoethenyl]-15-[[3-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.14,7]actadecane (215120-40-4)

Guidance literature:

Multi-step reaction with 17 steps

1: ZnI₂ / CH₂Cl₂ / 5.5 h / 20 °C

2: LiAlH₄ / tetrahydrofuran / 0 °C

3: imidazole / dimethylformamide / 0 °C

4: 93 percent / m-CPBA / CH₂Cl₂ / -60 °C

5: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 30 min

6: 65 percent / p-TsOH*H₂O, MeOH / 72 h / 25 °C

7: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 20 min, 2.) CH₂Cl₂, from -60 deg C to 0 deg C

8: 92 percent / DDQ / CH₂Cl₂ / 2.5 h / 20 °C

9: aq. NaClO₂, aq. NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.33 h / 0 °C

10: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 20 deg C, 10 h, 2.) toluene, 60 deg C, 1 h

11: OsO₄, NMO / dioxane; H₂O / 31 h / 20 °C

12: aq. NaIO₄ / dioxane / 0.67 h

13: H₂ / Pd/C / methanol / 0.67 h / 20 °C

14: 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

15: CrCl₂ / tetrahydrofuran / 0.5 h / 0 °C

16: aq. TFA / tetrahydrofuran / 6.5 h / 20 °C

17: NBS, 4A MS / acetonitrile / 0.08 h / -20 °C

With 1H-imidazole; 2,6-dimethylpyridine; chromium dichloride; methanol; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; N-Bromosuccinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 2-methyl-but-2-ene; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; hydrogen; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) iodide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

DOI:10.1021/ja982431b

upstream raw materials:

(2S,3R,4R,5S,6S)-3-Benzyloxy-6-((2R,3R,4S,5R)-3,5-dimethoxy-2-phenylsulfanyl-tetrahydro-pyran-4-yloxy)-4,5-dimethoxy-2-methyl-tetrahydro-pyran

(1S,4R,5R,7R,9R,13S,14R,15S)-4,15-dihydroxy-3,11-dioxo-9-[(E)-2-iodoethenyl]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]octadecane

3-[4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thiophenyl-β-D-xylopyranose

(2S,4S)-5,5-dimethyl-2-(4-methoxyphenyl)-1,3-dioxan-4-carboxaldehyde