(alphaS)-2-(3E)-3-Penten-1-yl-alpha-[2-(triphenylmethoxy)ethyl]-1,3-dithiane-2-ethanol

Base Information

• Chemical Name: (alphaS)-2-(3E)-3-Penten-1-yl-alpha-[2-(triphenylmethoxy)ethyl]-1,3-dithiane-2-ethanol
• CAS No.: 248582-05-0
• Molecular Formula: C₃₂H₃₈O₂S₂
• Molecular Weight: 518.785
• DSSTox Substance ID: DTXSID701137182
• Mol file: 248582-05-0.mol

Synonyms:DTXSID701137182;(alphaS)-2-(3E)-3-Penten-1-yl-alpha-[2-(triphenylmethoxy)ethyl]-1,3-dithiane-2-ethanol;248582-05-0

Chemical Property of (alphaS)-2-(3E)-3-Penten-1-yl-alpha-[2-(triphenylmethoxy)ethyl]-1,3-dithiane-2-ethanol

Chemical Property:

• XLogP3: 8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 12
• Exact Mass: 518.23132280
• Heavy Atom Count: 36
• Complexity: 581

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC=CCCC1(SCCCS1)CC(CCOC(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)O
• Isomeric SMILES: C/C=C/CCC1(SCCCS1)C[C@H](CCOC(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)O

Technology Process of (alphaS)-2-(3E)-3-Penten-1-yl-alpha-[2-(triphenylmethoxy)ethyl]-1,3-dithiane-2-ethanol

There total 2 articles about (alphaS)-2-(3E)-3-Penten-1-yl-alpha-[2-(triphenylmethoxy)ethyl]-1,3-dithiane-2-ethanol 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: 56.0%

2-(pent-trans-3-enyl)-[1,3]-dithiane (241819-10-3) + (3S)-3,4-epoxybutanyl triphenylmethyl ether → (+)-(2S)-1-{2-[(E)-pent-3-enyl]-1,3-dithian-2-yl}-4-(trityloxy)butan-2-ol (248582-05-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 168000h;

DOI:10.1002/(SICI)1522-2675(19990707)82:7<1111::AID-HLCA1111>3.0.CO;2-L

Reference yield:

trans-4-hexenal (25166-87-4) → (+)-(2S)-1-{2-[(E)-pent-3-enyl]-1,3-dithian-2-yl}-4-(trityloxy)butan-2-ol (248582-05-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 57 percent / 4-Angstroem molecular sieves; BF₃*OEt₂ / CH₂Cl₂ / 1.5 h / 0 °C

2: 56 percent / 1.6M BuLi / tetrahydrofuran / 168000 h / 0 °C

With n-butyllithium; 4 A molecular sieve; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; 1: Condensation / 2: Substitution;

DOI:10.1002/(SICI)1522-2675(19990707)82:7<1111::AID-HLCA1111>3.0.CO;2-L

Reference yield:

(+)-(2S)-1-{2-[(E)-pent-3-enyl]-1,3-dithian-2-yl}-4-(trityloxy)butan-2-ol (248582-05-0) → (3R,5S,8E)-5-[(benzyloxy)amino]dec-8-ene-1,3-diol (248582-10-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 40 percent / TsOH / methanol / 24 h / 20 °C

2: 57 percent / Hg(ClO₄)2*3H₂O / tetrahydrofuran; CHCl₃ / 0.08 h / 20 °C

3: pyridine; tetrahydrofuran / 20 h / 20 °C

4: tetramethylammonium triacetoxyboronhydride / acetic acid; acetonitrile / 5 h / -15 °C

With mercury(II) perchlorate; toluene-4-sulfonic acid; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; pyridine; methanol; chloroform; acetic acid; acetonitrile; 1: Hydrolysis / 2: ether cleavage / 3: Condensation / 4: Reduction;

DOI:10.1002/(SICI)1522-2675(19990707)82:7<1111::AID-HLCA1111>3.0.CO;2-L

upstream raw materials:

2-(pent-trans-3-enyl)-[1,3]-dithiane

trans-4-hexenal

Downstream raw materials:

(3S,8E)-1,3-dihydroxydec-8-en-5-one

(+)-(3R,5Z,8E)-1,3-dihydroxydec-8-en-5-one O-benzyloxime

(+)-(3R,5E,8E)-1,3-dihydroxydec-8-en-5-one O-benzyloxime

(3R,5S,8E)-5-[(benzyloxy)amino]dec-8-ene-1,3-diol