(diethoxy-phosphoryl)-acetic acid 4-{6-[4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl ester

Base Information

• Chemical Name: (diethoxy-phosphoryl)-acetic acid 4-{6-[4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl ester
• CAS No.: 471923-95-2
• Molecular Formula: C₅₇H₉₃O₁₃PSi₂
• Molecular Weight: 1073.5
• Mol file: 471923-95-2.mol

Synonyms:(diethoxy-phosphoryl)-acetic acid 4-{6-[4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl ester

Chemical Property of (diethoxy-phosphoryl)-acetic acid 4-{6-[4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (diethoxy-phosphoryl)-acetic acid 4-{6-[4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl ester

There total 18 articles about (diethoxy-phosphoryl)-acetic acid 4-{6-[4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl 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:

t-butyldimethylsiyl triflate (69739-34-0) → (diethoxy-phosphoryl)-acetic acid 4-{6-[4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl ester (471923-95-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 °C

2.1: 91 percent / 4,4'-di-tert-butylbiphenyl; Li / tetrahydrofuran / -78 °C

3.1: 97 percent / oxalyl chloride; dimethyl sulfoxide; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C

4.2: 88 percent / tetrahydrofuran; toluene / -78 - 20 °C

5.1: t-BuLi / diethyl ether; pentane / -78 - -45 °C

5.2: 2-thienylcyanocuprate / diethyl ether; tetrahydrofuran; pentane / -78 - 45 °C

5.3: 77 percent / diethyl ether; tetrahydrofuran; pentane / 1.75 h / -45 - 0 °C

6.1: 94 percent / DCC; DMAP / CH₂Cl₂ / 0.5 h / 20 °C

With 2,6-dimethylpyridine; dmap; oxalyl dichloride; 4,4'-di-tert-butylbiphenyl; tert.-butyl lithium; lithium; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; pentane; 3.1: Swern oxidation / 4.2: Julia olefination / 6.1: Mitsunobu reaction;

DOI:10.1021/ja020635t

Reference yield:

(1R,2S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)-2-((4-methoxybenzyl)oxy)ethan-1-ol (152386-85-1) → (diethoxy-phosphoryl)-acetic acid 4-{6-[4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl ester (471923-95-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / tetrahydrofuran

2.1: H₂SO₄ / methanol

3.1: PPh₃; DEAD / benzene / 0 °C

3.2: 150 °C / 1 Torr

4.1: t-BuLi / diethyl ether; pentane / -78 - -45 °C

4.2: 2-thienylcyanocuprate / diethyl ether; tetrahydrofuran; pentane / -78 - 45 °C

4.3: 77 percent / diethyl ether; tetrahydrofuran; pentane / 1.75 h / -45 - 0 °C

5.1: 94 percent / DCC; DMAP / CH₂Cl₂ / 0.5 h / 20 °C

With dmap; sulfuric acid; tert.-butyl lithium; sodium hydride; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; pentane; benzene; 5.1: Mitsunobu reaction;

DOI:10.1021/ja020635t

Reference yield:

(R)-ethyl 6-(benzyloxy)-5-hydroxyhex-2-ynoate (197520-87-9) → (diethoxy-phosphoryl)-acetic acid 4-{6-[4,8-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl ester (471923-95-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: CuI / tetrahydrofuran; diethyl ether / 0.17 h / 0 °C

1.2: 78 percent / tetrahydrofuran; diethyl ether / 1.17 h / -78 °C

2.1: 96 percent / DIBAL-H / tetrahydrofuran; toluene / -78 - 0 °C

3.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -78 °C

4.1: 91 percent / 4,4'-di-tert-butylbiphenyl; Li / tetrahydrofuran / -78 °C

5.1: 97 percent / oxalyl chloride; dimethyl sulfoxide; Et₃N / CH₂Cl₂ / -78 - 0 °C

6.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 0.5 h / -78 °C

6.2: 88 percent / tetrahydrofuran; toluene / -78 - 20 °C

7.1: t-BuLi / diethyl ether; pentane / -78 - -45 °C

7.2: 2-thienylcyanocuprate / diethyl ether; tetrahydrofuran; pentane / -78 - 45 °C

7.3: 77 percent / diethyl ether; tetrahydrofuran; pentane / 1.75 h / -45 - 0 °C

8.1: 94 percent / DCC; DMAP / CH₂Cl₂ / 0.5 h / 20 °C

With 2,6-dimethylpyridine; dmap; copper(l) iodide; oxalyl dichloride; 4,4'-di-tert-butylbiphenyl; tert.-butyl lithium; lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; pentane; 1.1: Michael addition / 5.1: Swern oxidation / 6.2: Julia olefination / 8.1: Mitsunobu reaction;

DOI:10.1021/ja020635t

upstream raw materials:

t-butyldimethylsiyl triflate

(1R,2S)-1-((R)-2,2-diethyl-1,3-dioxolan-4-yl)-2-((4-methoxybenzyl)oxy)ethan-1-ol

(R)-ethyl 6-(benzyloxy)-5-hydroxyhex-2-ynoate

(Z)-(R)-6-Benzyloxy-3-methyl-hex-2-ene-1,5-diol

Downstream raw materials:

(diethoxy-phosphoryl)-acetic acid 4-{6-[4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-8-oxo-octa-2,6-dienyl]-4-methylene-tetrahydro-pyran-2-yl}-1-[2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-but-3-enyl ester

(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-5-[(R)-2-(3,4-dimethoxy-benzyloxy)-1-(4-methoxy-benzyloxy)-ethyl]-3,11-dimethyl-19-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-7-one

[[13-(tert-butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]heneicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-hexa-2,4-dienoyl-carbamic acid 2-trimethylsilanyl-ethyl ester

[(S)-[(2E,8E,10Z,14E)-(1R,5R,13R,17R)-13-(tert-Butyl-dimethyl-silanyloxy)-3,11-dimethyl-19-methylene-7-oxo-6,21-dioxa-bicyclo[15.3.1]henicosa-2,8,10,14-tetraen-5-yl]-(4-methoxy-benzyloxy)-methyl]-carbamic acid 2-trimethylsilanyl-ethyl ester