(Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-yl tert-butyldimethylsilyl ether

Base Information

• Chemical Name: (Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-yl tert-butyldimethylsilyl ether
• CAS No.: 444682-16-0
• Molecular Formula: C₃₀H₅₂O₅Si
• Molecular Weight: 520.825
• Mol file: 444682-16-0.mol

Synonyms:(Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-yl tert-butyldimethylsilyl ether

Chemical Property of (Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-yl tert-butyldimethylsilyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-yl tert-butyldimethylsilyl ether

There total 13 articles about (Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-yl tert-butyldimethylsilyl ether 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: 81.0%

{4-[(tetrahydropyran-2-yl)oxy]butyl}(triphenyl)phosphonium iodide (90369-06-5) + (-)-(2R,3R,4S)-5-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal (261968-20-1) → (Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-yl tert-butyldimethylsilyl ether (444682-16-0)

Guidance literature:

{4-[(tetrahydropyran-2-yl)oxy]butyl}(triphenyl)phosphonium iodide; With NaNMDS; In tetrahydrofuran; benzene; at 20 ℃; for 0.833333h;

(-)-(2R,3R,4S)-5-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal; In tetrahydrofuran; benzene; at 20 ℃; for 5h; Further stages.;

DOI:10.1021/ol026084t

Reference yield: 67.0%

4-tetrahydropyranyloxybutanal (54911-85-2) + [(2R,3R,4S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl]-triphenyl-phosphonium; iodide → (Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-yl tert-butyldimethylsilyl ether (444682-16-0)

Guidance literature:

[(2R,3R,4S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,4-dimethyl-pentyl]-triphenyl-phosphonium; iodide; With sodium hexamethyldisilazane; at -78 - 20 ℃;

4-tetrahydropyranyloxybutanal;

DOI:10.1016/S0968-0896(03)00186-X

Reference yield:

(R)-3-(tert-butyldimethylsilyloxy)-2-methylpropan-1-ol (112057-64-4) → (Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethyl-9-(tetrahydropyran-2-yloxy)non-5-en-1-yl tert-butyldimethylsilyl ether (444682-16-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: molecular sieves 4 Angstroem / toluene / 0.33 h / 20 °C

2.2: 13.1 g / toluene / 3 h / -78 °C

3.1: 89 percent / NaH / tetrahydrofuran; dimethylformamide / 48 h / 20 °C

4.1: ozone; pyridine / CH₂Cl₂; methanol / -78 °C

4.2: dimethyl sulfide / CH₂Cl₂; methanol / -78 - 20 °C

5.1: NaHMDS / tetrahydrofuran / 0.83 h / 20 °C

5.2: 0.55 g / tetrahydrofuran / -78 - 20 °C

With pyridine; oxalyl dichloride; 4 A molecular sieve; sodium hexamethyldisilazane; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Swern oxidation / 5.2: Wittig reaction;

DOI:10.1016/S0968-0896(03)00186-X

upstream raw materials:

{4-[(tetrahydropyran-2-yl)oxy]butyl}(triphenyl)phosphonium iodide

(-)-(2R,3R,4S)-5-(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4-dimethylpentanal

4-tetrahydropyranyloxybutanal

2-(4-iodobutoxy)tetrahydropyran

Downstream raw materials:

(4-methoxybenzyloxy)acetic acid (Z,Z,Z)-(6S,7S,8S,13R,14S,15S,16S)-15-carbamoyloxy-7,13-bis(4-methoxybenzyloxy)-6,8,14,16-tetramethyleicosa-4,9,17,19-tetraenyl ester

(4-methoxybenzyloxy)acetic acid (Z,Z,Z)-(6S,7S,8S,13S,14S,15S,16S)-15-carbamoyloxy-7,13-bis(4-methoxybenzyloxy)-6,8,14,16-tetramethyleicosa-4,9,17,19-tetraenyl ester

tert-Butyl-[(4Z,9Z)-(1R,6S,7S,8S)-7-(4-methoxy-benzyloxy)-1-[(Z)-(1R,2S,3S)-2-(4-methoxy-benzyloxy)-1,3-dimethyl-hepta-4,6-dienyl]-6,8-dimethyl-13-(tetrahydro-pyran-2-yloxy)-trideca-4,9-dienyloxy]-dimethyl-silane

(Z,Z,Z)-(6S,7S,8S,13R,14S,15S,16S)-15-(tert-butyldimethylsilanyloxy)-7,13-bis(4-methoxybenzyloxy)-6,8,14,16-tetramethyleicosa-4,9,17,19-tetraen-1-yl tetrahydropyran-2-yl ether