[2-Chloro-5-((2E,4E)-(R)-6-{2-[(E)-(2S,3S,6S)-8,8-diethoxy-6-hydroxy-2-(2-methoxy-ethoxymethoxy)-3,5-dimethyl-oct-4-enyl]-[1,3]dithian-2-yl}-6-methoxy-2-methyl-hexa-2,4-dienyl)-3-methoxy-phenyl]-methyl-carbamic acid methyl ester

Base Information

• Chemical Name: [2-Chloro-5-((2E,4E)-(R)-6-{2-[(E)-(2S,3S,6S)-8,8-diethoxy-6-hydroxy-2-(2-methoxy-ethoxymethoxy)-3,5-dimethyl-oct-4-enyl]-[1,3]dithian-2-yl}-6-methoxy-2-methyl-hexa-2,4-dienyl)-3-methoxy-phenyl]-methyl-carbamic acid methyl ester
• CAS No.: 1053749-61-3
• Molecular Formula: C₄₀H₆₄ClNO₁₀S₂
• Molecular Weight: 818.534
• Mol file: 1053749-61-3.mol

Synonyms:[2-Chloro-5-((2E,4E)-(R)-6-{2-[(E)-(2S,3S,6S)-8,8-diethoxy-6-hydroxy-2-(2-methoxy-ethoxymethoxy)-3,5-dimethyl-oct-4-enyl]-[1,3]dithian-2-yl}-6-methoxy-2-methyl-hexa-2,4-dienyl)-3-methoxy-phenyl]-methyl-carbamic acid methyl ester

Chemical Property of [2-Chloro-5-((2E,4E)-(R)-6-{2-[(E)-(2S,3S,6S)-8,8-diethoxy-6-hydroxy-2-(2-methoxy-ethoxymethoxy)-3,5-dimethyl-oct-4-enyl]-[1,3]dithian-2-yl}-6-methoxy-2-methyl-hexa-2,4-dienyl)-3-methoxy-phenyl]-methyl-carbamic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2-Chloro-5-((2E,4E)-(R)-6-{2-[(E)-(2S,3S,6S)-8,8-diethoxy-6-hydroxy-2-(2-methoxy-ethoxymethoxy)-3,5-dimethyl-oct-4-enyl]-[1,3]dithian-2-yl}-6-methoxy-2-methyl-hexa-2,4-dienyl)-3-methoxy-phenyl]-methyl-carbamic acid methyl ester

There total 6 articles about [2-Chloro-5-((2E,4E)-(R)-6-{2-[(E)-(2S,3S,6S)-8,8-diethoxy-6-hydroxy-2-(2-methoxy-ethoxymethoxy)-3,5-dimethyl-oct-4-enyl]-[1,3]dithian-2-yl}-6-methoxy-2-methyl-hexa-2,4-dienyl)-3-methoxy-phenyl]-methyl-carbamic 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: 86.0%

C46H78ClNO10S2Si (1053634-29-9) → [2-Chloro-5-((2E,4E)-(R)-6-{2-[(E)-(2S,3S,6S)-8,8-diethoxy-6-hydroxy-2-(2-methoxy-ethoxymethoxy)-3,5-dimethyl-oct-4-enyl]-[1,3]dithian-2-yl}-6-methoxy-2-methyl-hexa-2,4-dienyl)-3-methoxy-phenyl]-methyl-carbamic acid methyl ester (1053749-61-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 50 ℃; for 48h;

DOI:10.1021/jo960363a

Reference yield:

tert-Butyl-[(E)-(1S,4S,5S)-1-(2,2-diethoxy-ethyl)-6-[1,3]dithian-2-yl-5-(2-methoxy-ethoxymethoxy)-2,4-dimethyl-hex-2-enyloxy]-dimethyl-silane → [2-Chloro-5-((2E,4E)-(R)-6-{2-[(E)-(2S,3S,6S)-8,8-diethoxy-6-hydroxy-2-(2-methoxy-ethoxymethoxy)-3,5-dimethyl-oct-4-enyl]-[1,3]dithian-2-yl}-6-methoxy-2-methyl-hexa-2,4-dienyl)-3-methoxy-phenyl]-methyl-carbamic acid methyl ester (1053749-61-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) TMEDA, n-BuLi / 1) hexane, THF, -20 deg C, 3 h; 2) hexane, THF, 0 deg C, 30 min

2: 1.) LDA, 2.) ZnCl₂ / 1) DME, heptane, -78 deg C, 30 min; 2) ether, -78 deg C, 1 h; 3) DME, heptane, -78 deg C, 1 h

3: 98 percent / Ag₂O / ethyl acetate / 1.5 h / 60 °C

4: 86 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 48 h / 50 °C

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; zinc(II) chloride; silver(l) oxide; lithium diisopropyl amide; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jo960363a

Reference yield:

2-[(E)-(2S,3S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-8,8-diethoxy-2-(2-methoxy-ethoxymethoxy)-3,5-dimethyl-oct-4-enyl]-[1,3]dithiane-2-carbaldehyde (1026598-10-6) → [2-Chloro-5-((2E,4E)-(R)-6-{2-[(E)-(2S,3S,6S)-8,8-diethoxy-6-hydroxy-2-(2-methoxy-ethoxymethoxy)-3,5-dimethyl-oct-4-enyl]-[1,3]dithian-2-yl}-6-methoxy-2-methyl-hexa-2,4-dienyl)-3-methoxy-phenyl]-methyl-carbamic acid methyl ester (1053749-61-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LDA, 2.) ZnCl₂ / 1) DME, heptane, -78 deg C, 30 min; 2) ether, -78 deg C, 1 h; 3) DME, heptane, -78 deg C, 1 h

2: 98 percent / Ag₂O / ethyl acetate / 1.5 h / 60 °C

3: 86 percent / tetrabutyl ammonium fluoride / tetrahydrofuran / 48 h / 50 °C

With tetrabutyl ammonium fluoride; zinc(II) chloride; silver(l) oxide; lithium diisopropyl amide; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jo960363a

upstream raw materials:

C₄₆H₇₈ClNO₁₀S₂Si

[5-((E)-4-Bromo-2-methyl-but-2-enyl)-2-chloro-3-methoxy-phenyl]-methyl-carbamic acid methyl ester

{2-Chloro-3-methoxy-5-[(E)-2-methyl-5-((S)-toluene-4-sulfinyl)-pent-2-enyl]-phenyl}-methyl-carbamic acid methyl ester

2-[(E)-(2S,3S,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-8,8-diethoxy-2-(2-methoxy-ethoxymethoxy)-3,5-dimethyl-oct-4-enyl]-[1,3]dithiane-2-carbaldehyde

Downstream raw materials:

(-)-maytansinol

(E)-(3S,6S,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-8-{2-[(2E,4E)-(R)-6-(4-chloro-3-methoxy-5-methylamino-phenyl)-1-methoxy-5-methyl-hexa-2,4-dienyl]-[1,3]dithian-2-yl}-7-(2-methoxy-ethoxymethoxy)-4,6-dimethyl-oct-4-enoic acid

(E)-(3S,6S,7S)-3-(tert-Butyl-dimethyl-silanyloxy)-8-(2-{(2E,4E)-(R)-6-[4-chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-1-methoxy-5-methyl-hexa-2,4-dienyl}-[1,3]dithian-2-yl)-7-(2-methoxy-ethoxymethoxy)-4,6-dimethyl-oct-4-enoic acid

(E)-(3S,6S,7S)-8-(2-{(2E,4E)-(R)-6-[4-Chloro-3-methoxy-5-(methoxycarbonyl-methyl-amino)-phenyl]-1-methoxy-5-methyl-hexa-2,4-dienyl}-[1,3]dithian-2-yl)-3-hydroxy-7-(2-methoxy-ethoxymethoxy)-4,6-dimethyl-oct-4-enoic acid