(2R,5Z)-N-{(1S,2R)-2-[(tert-butyl)dimethylsilyloxy]-1-({6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(3-methylbut-2-enyl)-β-D-galactopyranosyloxy}methyl)-9-[(1R,2S)-2-decylcyclopropyl]nonyl}-2-hydroxydec-5-enamide

Base Information

• Chemical Name: (2R,5Z)-N-{(1S,2R)-2-[(tert-butyl)dimethylsilyloxy]-1-({6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(3-methylbut-2-enyl)-β-D-galactopyranosyloxy}methyl)-9-[(1R,2S)-2-decylcyclopropyl]nonyl}-2-hydroxydec-5-enamide
• CAS No.: 304856-91-5
• Molecular Formula: C₈₂H₁₄₁NO₉Si₂
• Molecular Weight: 1341.19

Synonyms:(2R,5Z)-N-{(1S,2R)-2-[(tert-butyl)dimethylsilyloxy]-1-({6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(3-methylbut-2-enyl)-β-D-galactopyranosyloxy}methyl)-9-[(1R,2S)-2-decylcyclopropyl]nonyl}-2-hydroxydec-5-enamide

Chemical Property of (2R,5Z)-N-{(1S,2R)-2-[(tert-butyl)dimethylsilyloxy]-1-({6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(3-methylbut-2-enyl)-β-D-galactopyranosyloxy}methyl)-9-[(1R,2S)-2-decylcyclopropyl]nonyl}-2-hydroxydec-5-enamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2R,5Z)-N-{(1S,2R)-2-[(tert-butyl)dimethylsilyloxy]-1-({6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(3-methylbut-2-enyl)-β-D-galactopyranosyloxy}methyl)-9-[(1R,2S)-2-decylcyclopropyl]nonyl}-2-hydroxydec-5-enamide

There total 16 articles about (2R,5Z)-N-{(1S,2R)-2-[(tert-butyl)dimethylsilyloxy]-1-({6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(3-methylbut-2-enyl)-β-D-galactopyranosyloxy}methyl)-9-[(1R,2S)-2-decylcyclopropyl]nonyl}-2-hydroxydec-5-enamide 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: 86.0%

(2R,5Z)-2-[(tert-butyl)dimethylsilyloxy]-10-[(1R,2S)-2-decylcyclopropyl]dec-5-enoic acid (304856-79-9) + (2S,3R)-2-amino-3-[(tert-butyl)dimethylsilyloxy]-1-{6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(3-methylbut-2-enyl)-β-D-galactopyranosyloxy}-10-[(1R,2S)-2-decylcyclopropyl]decane → (2R,5Z)-N-{(1S,2R)-2-[(tert-butyl)dimethylsilyloxy]-1-({6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(3-methylbut-2-enyl)-β-D-galactopyranosyloxy}methyl)-9-[(1R,2S)-2-decylcyclopropyl]nonyl}-2-hydroxydec-5-enamide (304856-91-5)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; at 0 ℃; for 5h;

DOI:10.1002/1522-2675(20000809)83:8<1977::AID-HLCA1977>3.0.CO;2-D

Reference yield:

tridec-2-yn-1-ol (51887-25-3) → (2R,5Z)-N-{(1S,2R)-2-[(tert-butyl)dimethylsilyloxy]-1-({6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(3-methylbut-2-enyl)-β-D-galactopyranosyloxy}methyl)-9-[(1R,2S)-2-decylcyclopropyl]nonyl}-2-hydroxydec-5-enamide (304856-91-5)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 96 percent / H₂ / Pd/BaSO₄ / pyridine / 10 h / 25 °C / 760 Torr

2.1: Zn(CH₂I)2*DME / CH₂Cl₂ / 6 h / -15 - 25 °C

3.1: 96 percent / I₂; imidazole; Ph₃P / acetonitrile; diethyl ether / 1 h / 0 °C

4.1: Mg / tetrahydrofuran

4.2: 84 percent / Li₂CuCl₂ / tetrahydrofuran / 0.5 h / 0 °C

5.1: 100 percent / PPTS / methanol / 5 h / 55 °C

6.1: 97 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 25 °C

7.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.25 h / 0 °C

7.2: 97 percent / tetrahydrofuran / 0.75 h / 0 °C

8.1: 91 percent / K₃(FeCN)6; MeSO₂NH₂K₂Os₂(OH)4; (DHQD)2AQN / 2-methyl-propan-2-ol; H₂O / 8 h / 0 °C

9.1: 91 percent / pyridine / 0.67 h / 25 °C

10.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 - 25 °C

11.1: 100 percent / DIBAL / CH₂Cl₂ / 0.33 h / -78 °C

12.1: 100 percent / H₂ / Lindlar catalyst / ethanol / 0.5 h / 25 °C / 760 Torr

13.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 25 °C

14.1: 95 percent / 2-methylbut-2-ene; NaH₂PO₄; NaCl₂O / 2-methyl-propan-2-ol; tetrahydrofuran / 0.5 h / 0 °C

15.1: 86 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 5 h / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium dihydrogenphosphate; 1-hydroxy-7-aza-benzotriazole; 2-methyl-but-2-ene; oxalyl dichloride; hydroquinidine anthraquinone-1,4-diyl diether; MeSO₂NH₂K₂Os₂(OH)4; hydrogen; iodine; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; magnesium; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; (ICH₂)2Zn dimethoxyethane complex; potassium hexacyanoferrate(III); Pd-BaSO₄; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; acetonitrile; tert-butyl alcohol; 1.1: Catalytic hydrogenation / 2.1: cyclopropanation / 3.1: Iodination / 4.1: Metallation / 4.2: Grignard reaction / 5.1: ether cleavage / 6.1: Swern oxidation / 7.1: deprotonation / 7.2: Wittig olefination / 8.1: Sharpless asymmetric dihydroxylation / 9.1: Esterification / 10.1: silylation / 11.1: Reduction / 12.1: Catalytic hydrogenation / 13.1: Oxidation / 14.1: Oxidation / 15.1: Condensation;

DOI:10.1002/1522-2675(20000809)83:8<1977::AID-HLCA1977>3.0.CO;2-D

Reference yield:

(Z)-tridec-2-en-1-ols (74962-99-5,68480-25-1) → (2R,5Z)-N-{(1S,2R)-2-[(tert-butyl)dimethylsilyloxy]-1-({6-O-[(tert-butyl)diphenylsilyl]-3,4-O-isopropylidene-2-O-(3-methylbut-2-enyl)-β-D-galactopyranosyloxy}methyl)-9-[(1R,2S)-2-decylcyclopropyl]nonyl}-2-hydroxydec-5-enamide (304856-91-5)

Guidance literature:

Multi-step reaction with 14 steps

1.1: Zn(CH₂I)2*DME / CH₂Cl₂ / 6 h / -15 - 25 °C

2.1: 96 percent / I₂; imidazole; Ph₃P / acetonitrile; diethyl ether / 1 h / 0 °C

3.1: Mg / tetrahydrofuran

3.2: 84 percent / Li₂CuCl₂ / tetrahydrofuran / 0.5 h / 0 °C

4.1: 100 percent / PPTS / methanol / 5 h / 55 °C

5.1: 97 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 25 °C

6.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.25 h / 0 °C

6.2: 97 percent / tetrahydrofuran / 0.75 h / 0 °C

7.1: 91 percent / K₃(FeCN)6; MeSO₂NH₂K₂Os₂(OH)4; (DHQD)2AQN / 2-methyl-propan-2-ol; H₂O / 8 h / 0 °C

8.1: 91 percent / pyridine / 0.67 h / 25 °C

9.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / -78 - 25 °C

10.1: 100 percent / DIBAL / CH₂Cl₂ / 0.33 h / -78 °C

11.1: 100 percent / H₂ / Lindlar catalyst / ethanol / 0.5 h / 25 °C / 760 Torr

12.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 25 °C

13.1: 95 percent / 2-methylbut-2-ene; NaH₂PO₄; NaCl₂O / 2-methyl-propan-2-ol; tetrahydrofuran / 0.5 h / 0 °C

14.1: 86 percent / 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 5 h / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium dihydrogenphosphate; 1-hydroxy-7-aza-benzotriazole; 2-methyl-but-2-ene; oxalyl dichloride; hydroquinidine anthraquinone-1,4-diyl diether; MeSO₂NH₂K₂Os₂(OH)4; hydrogen; iodine; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; magnesium; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; triphenylphosphine; (ICH₂)2Zn dimethoxyethane complex; potassium hexacyanoferrate(III); Lindlar's catalyst; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; acetonitrile; tert-butyl alcohol; 1.1: cyclopropanation / 2.1: Iodination / 3.1: Metallation / 3.2: Grignard reaction / 4.1: ether cleavage / 5.1: Swern oxidation / 6.1: deprotonation / 6.2: Wittig olefination / 7.1: Sharpless asymmetric dihydroxylation / 8.1: Esterification / 9.1: silylation / 10.1: Reduction / 11.1: Catalytic hydrogenation / 12.1: Oxidation / 13.1: Oxidation / 14.1: Condensation;

DOI:10.1002/1522-2675(20000809)83:8<1977::AID-HLCA1977>3.0.CO;2-D

upstream raw materials:

(2R,5Z)-2-[(tert-butyl)dimethylsilyloxy]-10-[(1R,2S)-2-decylcyclopropyl]dec-5-enoic acid

tridec-2-yn-1-ol

(Z)-tridec-2-en-1-ols

[(1R,2S)-2-decylcylopropyl]methanol

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