(1S,2S,3R)-1-{[(1S)-3,3-diethyl-2,4-dioxolanyl]methyl}-3-methoxy-1-[(4-methoxyphenyl)methoxy]-2-methyl-4-(1,1,2,2-tetramethyl-1-silapropoxy)butane

Base Information

• Chemical Name: (1S,2S,3R)-1-{[(1S)-3,3-diethyl-2,4-dioxolanyl]methyl}-3-methoxy-1-[(4-methoxyphenyl)methoxy]-2-methyl-4-(1,1,2,2-tetramethyl-1-silapropoxy)butane
• CAS No.: 207303-18-2
• Molecular Formula: C₂₈H₅₀O₆Si
• Molecular Weight: 510.787
• Mol file: 207303-18-2.mol

Synonyms:(1S,2S,3R)-1-{[(1S)-3,3-diethyl-2,4-dioxolanyl]methyl}-3-methoxy-1-[(4-methoxyphenyl)methoxy]-2-methyl-4-(1,1,2,2-tetramethyl-1-silapropoxy)butane

Chemical Property of (1S,2S,3R)-1-{[(1S)-3,3-diethyl-2,4-dioxolanyl]methyl}-3-methoxy-1-[(4-methoxyphenyl)methoxy]-2-methyl-4-(1,1,2,2-tetramethyl-1-silapropoxy)butane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R)-1-{[(1S)-3,3-diethyl-2,4-dioxolanyl]methyl}-3-methoxy-1-[(4-methoxyphenyl)methoxy]-2-methyl-4-(1,1,2,2-tetramethyl-1-silapropoxy)butane

There total 15 articles about (1S,2S,3R)-1-{[(1S)-3,3-diethyl-2,4-dioxolanyl]methyl}-3-methoxy-1-[(4-methoxyphenyl)methoxy]-2-methyl-4-(1,1,2,2-tetramethyl-1-silapropoxy)butane 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: 99.0%

p-Methoxybenzyl bromide (2746-25-0) + (2S,3S,4R)-1-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-3-methyl-5-(1,1,2,2-tetramethyl-1-silapropoxy)pentan-2-ol (207303-02-4) → (1S,2S,3R)-1-{[(1S)-3,3-diethyl-2,4-dioxolanyl]methyl}-3-methoxy-1-[(4-methoxyphenyl)methoxy]-2-methyl-4-(1,1,2,2-tetramethyl-1-silapropoxy)butane (207303-18-2)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; 0 deg C to rt;

DOI:10.1016/S0040-4039(98)00268-8

Reference yield:

(R)-2,2-diethyl-1,3-dioxolane-4-carboxaldehyde (120157-60-0) → (1S,2S,3R)-1-{[(1S)-3,3-diethyl-2,4-dioxolanyl]methyl}-3-methoxy-1-[(4-methoxyphenyl)methoxy]-2-methyl-4-(1,1,2,2-tetramethyl-1-silapropoxy)butane (207303-18-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: ZnBr₂ / tetrahydrofuran; diethyl ether / 1 h / 0 °C

1.2: tetrahydrofuran; diethyl ether / 48 h / 0 °C

2.1: 96 percent / pyridine / CH₂Cl₂ / 17 h / 0 - 25 °C

3.1: 83 percent / LiHMDS; Me₃SiCl; Et₃N / tetrahydrofuran / 17.5 h / -100 - 25 °C

4.1: 38 percent / NaHCO₃; NBS / CCl₄ / 20 h / 20 °C

5.1: 86 percent / n-Bu₃SnH; AIBN / benzene / 16 h / Heating

6.1: 91 percent / LiAlH₄ / tetrahydrofuran / 22.5 h / -78 - 20 °C

7.1: 94 percent / DMAP; Et₃N / CH₂Cl₂ / 18 h / 0 - 20 °C

8.1: 54 percent / Ph₃P; diethyl azodicarboxylate / benzene / 72 h / 20 °C

9.1: 96 percent / K₂CO₃ / methanol; diethyl ether; H₂O / 18 h / 20 °C

10.1: 99 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 3 h / 0 - 20 °C

With pyridine; dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sodium hydrogencarbonate; potassium carbonate; triethylamine; triphenylphosphine; zinc dibromide; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1.1: transmetallation / 1.2: Addition / 2.1: Esterification / 3.1: Ireland-Claisen rearrangement / 4.1: Cyclization / 5.1: Dehalogenation / 6.1: Reduction / 7.1: silylation / 8.1: Mitsunobu reaction / 9.1: Hydrolysis / 10.1: Etherification;

DOI:10.1021/jo980754k

Reference yield:

1-[(1R)-3,3-diethyl-2,4-dioxolanyl]but-2-yn-1-one (214462-03-0) → (1S,2S,3R)-1-{[(1S)-3,3-diethyl-2,4-dioxolanyl]methyl}-3-methoxy-1-[(4-methoxyphenyl)methoxy]-2-methyl-4-(1,1,2,2-tetramethyl-1-silapropoxy)butane (207303-18-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 389 mg / (R)-Alpine borane / tetrahydrofuran / 40 h / 20 °C

2: 97 percent / DMAP; Et₃N / 18.3 h / 0 - 20 °C

3: 70 percent / KH₂PO₄; air / porcine pancreatic lipase (EC 3.1.1.3) / H₂O / 6.5 h / 23 °C / pH 6.0

4: 98 percent / LiAlH₄ / tetrahydrofuran / 20.5 h / 0 - 20 °C / Heating

5: 96 percent / pyridine / CH₂Cl₂ / 17 h / 0 - 25 °C

6: 83 percent / LiHMDS; Me₃SiCl; Et₃N / tetrahydrofuran / 17.5 h / -100 - 25 °C

7: 38 percent / NaHCO₃; NBS / CCl₄ / 20 h / 20 °C

8: 86 percent / n-Bu₃SnH; AIBN / benzene / 16 h / Heating

9: 91 percent / LiAlH₄ / tetrahydrofuran / 22.5 h / -78 - 20 °C

10: 94 percent / DMAP; Et₃N / CH₂Cl₂ / 18 h / 0 - 20 °C

11: 54 percent / Ph₃P; diethyl azodicarboxylate / benzene / 72 h / 20 °C

12: 96 percent / K₂CO₃ / methanol; diethyl ether; H₂O / 18 h / 20 °C

13: 99 percent / NaHMDS / tetrahydrofuran; dimethylformamide / 3 h / 0 - 20 °C

With pyridine; dmap; potassium dihydrogenphosphate; N-Bromosuccinimide; lithium aluminium tetrahydride; chloro-trimethyl-silane; B-isopinocampheyl-9-borabicyclo[3.3.1]nonane; air; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sodium hydrogencarbonate; potassium carbonate; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; porcine pancreatic lipase (EC 3.1.1.3); In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene; 1: Reduction / 2: Acetylation / 3: Hydrolysis / 4: Reduction / 5: Esterification / 6: Ireland-Claisen rearrangement / 7: Cyclization / 8: Dehalogenation / 9: Reduction / 10: silylation / 11: Mitsunobu reaction / 12: Hydrolysis / 13: Etherification;

DOI:10.1021/jo980754k

upstream raw materials:

p-Methoxybenzyl bromide

(2S,3S,4R)-1-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-3-methyl-5-(1,1,2,2-tetramethyl-1-silapropoxy)pentan-2-ol

(R)-2,2-diethyl-1,3-dioxolane-4-carboxaldehyde

4-Methoxybenzyl alcohol

Downstream raw materials:

(4R,5S,6S)-methyl 7-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-6-[(4-methoxyphenyl)methoxy]-3,5-dimethylhept-2-enoate

(4R,5S,6S)-7-[(1S)-3,3-diethyl-2,4-dioxolanyl]-4-methoxy-6-[(4-methoxyphenyl)methoxy]-3,5-dimethylhept-2-enal

(3R,4S,5S)-6-[(1S)-3,3-diethyl-2,4-dioxolanyl]-3-methoxy-5-[(4-methoxyphenyl)methoxy]-4-methylhexan-2-one

(2R,3S,4S)-5-[(1S)-3,3-diethyl-2,4-dioxolanyl]-2-methoxy-4-[(4-methoxyphenyl)methoxy]-3-methylpentanal