(1S,4R,5R,7R,9R,13S,14S,15S)-4-hydroxy-9-[(E)-2-iodovinyl]-15-[[3-O-[4-O-(p-methoxybenzyl)-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]octadecane-3,11-dione

Base Information

• Chemical Name: (1S,4R,5R,7R,9R,13S,14S,15S)-4-hydroxy-9-[(E)-2-iodovinyl]-15-[[3-O-[4-O-(p-methoxybenzyl)-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]octadecane-3,11-dione
• CAS No.: 223693-28-5
• Molecular Formula: C₄₄H₆₅IO₁₆
• Molecular Weight: 976.895

Synonyms:(1S,4R,5R,7R,9R,13S,14S,15S)-4-hydroxy-9-[(E)-2-iodovinyl]-15-[[3-O-[4-O-(p-methoxybenzyl)-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]octadecane-3,11-dione

Chemical Property of (1S,4R,5R,7R,9R,13S,14S,15S)-4-hydroxy-9-[(E)-2-iodovinyl]-15-[[3-O-[4-O-(p-methoxybenzyl)-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]octadecane-3,11-dione

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Technology Process of (1S,4R,5R,7R,9R,13S,14S,15S)-4-hydroxy-9-[(E)-2-iodovinyl]-15-[[3-O-[4-O-(p-methoxybenzyl)-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]octadecane-3,11-dione

There total 37 articles about (1S,4R,5R,7R,9R,13S,14S,15S)-4-hydroxy-9-[(E)-2-iodovinyl]-15-[[3-O-[4-O-(p-methoxybenzyl)-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]octadecane-3,11-dione 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: 49.0%

(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) + (2S,3S,4R,5R,6S)-2-((3R,4S,5R)-3,5-Dimethoxy-2-phenylsulfanyl-tetrahydro-pyran-4-yloxy)-3,4-dimethoxy-5-(4-methoxy-benzyloxy)-6-methyl-tetrahydro-pyran → (1S,4R,5R,7R,9R,13S,14S,15S)-4-hydroxy-9-[(E)-2-iodovinyl]-15-[[3-O-[4-O-(p-methoxybenzyl)-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]octadecane-3,11-dione (223693-28-5)

Guidance literature:

With N-Bromosuccinimide; 4 A molecular sieve; In acetonitrile; at -20 - 0 ℃;

DOI:10.1021/ja990384x

Reference yield: 36.0%

(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) + phenyl 3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside (261374-44-1) → (1S,4R,5R,7R,9R,13S,14S,15S)-4-hydroxy-9-[(E)-2-iodovinyl]-15-[[3-O-[4-O-(p-methoxybenzyl)-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]octadecane-3,11-dione (223693-28-5) + (1S,4R,5R,7R,9R,13S,14S,15S)-4-hydroxy-9-[(E)-2-iodovinyl]-15-[[3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-α-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.14,7]octadecane-3,11-dione

Guidance literature:

With N-Bromosuccinimide; In acetonitrile;

DOI:10.1021/ja993487o

Reference yield:

(2R,4R)-5-formyl-4-[(p-methoxybenzyl)oxy]-2,5-dimethylhexyl pivalate (223693-00-3) → (1S,4R,5R,7R,9R,13S,14S,15S)-4-hydroxy-9-[(E)-2-iodovinyl]-15-[[3-O-[4-O-(p-methoxybenzyl)-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]octadecane-3,11-dione (223693-28-5)

Guidance literature:

Multi-step reaction with 20 steps

1.1: potassium hexamethyldisilazide / toluene; tetrahydrofuran / 0.33 h / 0 °C

1.2: 89 percent / tetrahydrofuran; toluene / 0.33 h / 0 °C

2.1: 99 percent / (DHQ)2PYR; OsO₄; K₃Fe(CN)6 / K₂CO₃ / H₂O; 2-methyl-propan-2-ol / 0 °C

3.1: 636 mg / imidazole / tetrahydrofuran / 5 h

4.1: 439 mg / DMAP; imidazole / dimethylformamide / 5 h

5.1: 79 percent / Dibal-H / tetrahydrofuran; hexane / 1 h / -40 °C

6.1: 89 percent / tetra-n-propylammonium perruthenate; NMO; 4A MS / CH₂Cl₂ / 1 h

7.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: 76 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C

8.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

9.1: 97 percent / p-TsOH / methanol / 1 h

10.1: OsO₄; NMO; water / tetrahydrofuran / 4 h

11.1: 89 percent / aq. NaIO₄ / tetrahydrofuran / 0.5 h

12.1: 88 percent / aq. NaH₂PO₄; NaClO₂; 2-methyl-2-butene / H₂O; 2-methyl-propan-2-ol / 0.17 h / 0 °C

13.1: NEt₃ / tetrahydrofuran / 4 h / 25 °C

14.1: 82 percent / DMAP / tetrahydrofuran; toluene / 0.5 h / 110 °C

15.1: 64 percent / HF*pyridine; THF*pyridine / 5 h / 20 °C

16.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

17.1: 54 mg / CrCl₂ / tetrahydrofuran / 3 h / 0 °C

18.1: Davis oxaziridine; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 1 h / 0 °C

19.1: 73 percent / DDQ / CH₂Cl₂; H₂O / 20 h

20.1: 36 percent / NBS; 4A MS / acetonitrile

With tetrahydrofuran; pyridine; 1H-imidazole; chromium dichloride; dmap; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; N-Bromosuccinimide; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); potassium tert-butylate; water; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; (+)-[(8,8-dichlorocamphoryl)sulfonyl]oxaziridine; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 1.1: Metallation / 1.2: Wittig olefination / 2.1: hydroxylation / 3.1: silylation / 4.1: silylation / 5.1: reductive deacylation / 6.1: Oxidation / 7.1: Metallation / 7.2: Addition / 8.1: Oxidation / 9.1: desilylation / 10.1: dihydroxylation / 11.1: oxidative cleavage / 12.1: Oxidation / 13.1: Condensation / 14.1: Cyclization / 15.1: desilylation / 16.1: Oxidation / 17.1: Takai iodovinylation / 18.1: oxidative desulfonylation / 19.1: transannular cyclization / 20.1: Nicolaou glycosidation;

DOI:10.1021/ja993487o

upstream raw materials:

(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

phenyl 3-O-[4-O-(p-methoxybenzyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside

p-methoxybenzyl chloride

phenyl 3-O-[4-O-(tert-butyldimethylsilyl)-2,3-di-O-methyl-α-L-fucopyranosyl]-2,4-di-O-methyl-1-thio-β-D-xylopyranoside

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