(1S,2S,4E)-acetic acid 1-allyl-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-enyl ester

Base Information

• Chemical Name: (1S,2S,4E)-acetic acid 1-allyl-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-enyl ester
• CAS No.: 331414-52-9
• Molecular Formula: C₃₂H₄₂O₅
• Molecular Weight: 506.682
• Mol file: 331414-52-9.mol

Synonyms:(1S,2S,4E)-acetic acid 1-allyl-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-enyl ester

Chemical Property of (1S,2S,4E)-acetic acid 1-allyl-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,4E)-acetic acid 1-allyl-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-enyl ester

There total 13 articles about (1S,2S,4E)-acetic acid 1-allyl-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-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: 96.0%

acetic anhydride (108-24-7) + (4S,5S,7E)-9-benzyloxy-5-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-nona-1,7-dien-4-ol (331414-64-3) → (1S,2S,4E)-acetic acid 1-allyl-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-enyl ester (331414-52-9)

Guidance literature:

With pyridine; dmap; In dichloromethane;

DOI:10.1021/ja005892h DOI:10.1016/S0040-4020(02)00040-6

Reference yield:

(4R)-4-benzyl-3-[2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-acetyl]-oxazolidin-2-one (289619-01-8) → (1S,2S,4E)-acetic acid 1-allyl-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-enyl ester (331414-52-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaN(SiMe₃)2 / toluene; tetrahydrofuran / 0.5 h / -78 °C

1.2: 75 percent / toluene; tetrahydrofuran / 2 h / -45 °C

2.1: 88 percent / NaBH₄; H₂O / tetrahydrofuran / 5 - 20 °C

3.1: (COCl)2; DMSO / CH₂Cl₂ / 0.42 h / -78 °C

4.1: methoxyborane derived from 3-carene / diethyl ether / 1 h / 20 °C

4.2: diethyl ether / 2 h / -78 °C

4.3: aq. NaOH; aq. H₂O₂ / diethyl ether; tetrahydrofuran / 3 h / 20 °C

5.1: 96 percent / pyridine; 4-dimethylaminopyridine / CH₂Cl₂

With pyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; methoxyborane derived from 3-carene; water; sodium hexamethyldisilazane; dimethyl sulfoxide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 3.1: Swern oxidation;

DOI:10.1016/S0040-4020(02)00040-6

Reference yield:

(4R)-4-benzyl-3-[(2S,4E)-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-enoyl]-oxazolidin-2-one (331414-49-4) → (1S,2S,4E)-acetic acid 1-allyl-6-benzyloxy-2-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-hex-4-enyl ester (331414-52-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 88 percent / NaBH₄; H₂O / tetrahydrofuran / 5 - 20 °C

2.1: (COCl)2; DMSO / CH₂Cl₂ / 0.42 h / -78 °C

3.1: methoxyborane derived from 3-carene / diethyl ether / 1 h / 20 °C

3.2: diethyl ether / 2 h / -78 °C

3.3: aq. NaOH; aq. H₂O₂ / diethyl ether; tetrahydrofuran / 3 h / 20 °C

4.1: 96 percent / pyridine; 4-dimethylaminopyridine / CH₂Cl₂

With pyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; methoxyborane derived from 3-carene; water; dimethyl sulfoxide; In tetrahydrofuran; diethyl ether; dichloromethane; 2.1: Swern oxidation;

DOI:10.1016/S0040-4020(02)00040-6

upstream raw materials:

acetic anhydride

(4S,5S,7E)-9-benzyloxy-5-((1R,2R)-2-benzyloxy-1-ethyl-pent-4-enyloxy)-nona-1,7-dien-4-ol

(3R,4R)-4-benzyloxy-hept-6-en-3-ol

(R)-(+)-2-Benzyloxypent-4-enal

Downstream raw materials:

2,4,6-triisopropyl-benzenesulfonic acid (1R)-1-((2R,3aS,5R,6R,10aS)-5-ethyl-6-triethylsilanyloxy-2,3,3a,5,6,7,10,10a-octahydro-furo[3,2-b]oxonin-2-yl)-prop-2-ynyl ester