(E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4-bis-ethylsulfanyl-butoxy]-acrylic acid methyl ester

Base Information

• Chemical Name: (E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4-bis-ethylsulfanyl-butoxy]-acrylic acid methyl ester
• CAS No.: 406684-06-8
• Molecular Formula: C₃₃H₅₀O₆S₂Si
• Molecular Weight: 634.974
• Mol file: 406684-06-8.mol

Synonyms:(E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4-bis-ethylsulfanyl-butoxy]-acrylic acid methyl ester

Chemical Property of (E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4-bis-ethylsulfanyl-butoxy]-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4-bis-ethylsulfanyl-butoxy]-acrylic acid methyl ester

There total 1 articles about (E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4-bis-ethylsulfanyl-butoxy]-acrylic 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: 87.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 2,3-di-O-benzyl-4,5-O-isopropylidene-L-arabinose diethyldithioacetal (75858-37-6) + propynoic acid methyl ester (922-67-8) → (E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4-bis-ethylsulfanyl-butoxy]-acrylic acid methyl ester (406684-06-8)

Guidance literature:

2,3-di-O-benzyl-4,5-O-isopropylidene-L-arabinose diethyldithioacetal; With hydrogenchloride; In methanol; at 0 - 20 ℃; for 8h;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In dichloromethane; at 20 ℃; for 0.166667h;

propynoic acid methyl ester; With 4-methyl-morpholine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1002/1521-3773(20020104)41:1<176::AID-ANIE176>3.0.CO;2-#

Reference yield: 79.0%

(E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4-bis-ethylsulfanyl-butoxy]-acrylic acid methyl ester (406684-06-8) → (E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-4-bromo-1-(tert-butyl-dimethyl-silanyloxymethyl)-butoxy]-acrylic acid methyl ester (406684-07-9)

Guidance literature:

(E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4-bis-ethylsulfanyl-butoxy]-acrylic acid methyl ester; With sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene; In water; acetonitrile; at 0 ℃; for 0.0833333h;

With sodium tetrahydroborate; In water; acetonitrile; at 0 ℃; for 0.5h;

With carbon tetrabromide; triethylamine; triphenylphosphine; In dichloromethane; at 0 - 20 ℃; for 2h;

DOI:10.1002/1521-3773(20020104)41:1<176::AID-ANIE176>3.0.CO;2-#

Reference yield:

(E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxymethyl)-4,4-bis-ethylsulfanyl-butoxy]-acrylic acid methyl ester (406684-06-8) → (+)-ambruticin S (58857-02-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: (C₆H₅)I(OCOCF₃)2; NaHCO₃ / acetonitrile; H₂O / 0.08 h / 0 °C

1.2: NaBH₄ / acetonitrile; H₂O / 0.5 h / 0 °C

1.3: 79 percent / CBr₄; P(C₆H₅)3; N(C₂H₅)3 / CH₂Cl₂ / 2 h / 0 - 20 °C

2.1: (C₄H₉)3Sn / AIBN / benzene / 2 h / Heating

3.1: HCl / methanol / 0.5 h / 0 - 20 °C

3.2: (COCl)2; DMSO / CH₂Cl₂ / 1 h / -78 °C

3.3: 67 percent / N(C₂H₅)3 / CH₂Cl₂ / 7 h / -78 °C

4.1: sodium hexamethyldisilazide / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -78 - 20 °C

5.1: HCl / methanol / 1 h / 20 °C

5.2: (COCl)2; DMSO / CH₂Cl₂ / 0.5 h / -78 °C

5.3: 62 percent / N(C₂H₅)3 / CH₂Cl₂ / -78 - 20 °C

6.1: NaN(Si(CH₃)3)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -60 - 0 °C

7.1: LiOH / tetrahydrofuran; H₂O / 8 h / 20 °C

7.2: 89 percent / Li / liquid ammonia; ethanol / 0.17 h / -78 °C

With lithium hydroxide; (C₄H₉)3Sn; sodium hexamethyldisilazane; sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene; hydrogenchloride; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; water; acetonitrile; benzene; 3.2: Swern oxidation / 4.1: Kocienski-Julia reaction / 5.2: Swern oxidation;

DOI:10.1002/1521-3773(20020104)41:1<176::AID-ANIE176>3.0.CO;2-#

upstream raw materials:

tert-butyldimethylsilyl chloride

2,3-di-O-benzyl-4,5-O-isopropylidene-L-arabinose diethyldithioacetal

propynoic acid methyl ester

Downstream raw materials:

(E)-3-[(1S,2S,3R)-2,3-Bis-benzyloxy-4-bromo-1-(tert-butyl-dimethyl-silanyloxymethyl)-butoxy]-acrylic acid methyl ester

(+)-ambruticin S

methyl (8E,10S,11S,12S)-2,3-di-O-benzyl-1,4-dideoxy-1β-<11-methyl-12-formylcyclopropylethenyl>-D-glucoheptopyranuronate

methyl 5β,6α-dibenzyloxypolyangioate