1,3-Dioxolan-2-one, 4-methyl-5-[3-(phenylmethoxy)propyl]-, (4S,5R)-

Base Information

• Chemical Name: 1,3-Dioxolan-2-one, 4-methyl-5-[3-(phenylmethoxy)propyl]-, (4S,5R)-
• CAS No.: 918819-00-8
• Molecular Formula: C14H18O4
• Molecular Weight: 250.295
• DSSTox Substance ID: DTXSID40474367
• Nikkaji Number: J1.811.682K
• Wikidata: Q82304349
• Mol file: 918819-00-8.mol

Synonyms:918819-00-8;1,3-Dioxolan-2-one, 4-methyl-5-[3-(phenylmethoxy)propyl]-, (4S,5R)-;DTXSID40474367

Chemical Property of 1,3-Dioxolan-2-one, 4-methyl-5-[3-(phenylmethoxy)propyl]-, (4S,5R)-

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 250.12050905
• Heavy Atom Count: 18
• Complexity: 261

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(OC(=O)O1)CCCOCC2=CC=CC=C2
• Isomeric SMILES: C[C@H]1[C@H](OC(=O)O1)CCCOCC2=CC=CC=C2

Technology Process of 1,3-Dioxolan-2-one, 4-methyl-5-[3-(phenylmethoxy)propyl]-, (4S,5R)-

There total 5 articles about 1,3-Dioxolan-2-one, 4-methyl-5-[3-(phenylmethoxy)propyl]-, (4S,5R)- 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: 43.0%

(4RS,5SR)-4-(3-benzyloxy)propyl-5-methyl-1,3-dioxolan-2-one → (2R,3S)-(6-benzyloxy)hexane-2,3-diol + (4R,5S)-4-(3-benzyloxy)propyl-5-methyl-1,3-dioxolan-2-one (918819-00-8)

Guidance literature:

With Pseudomonas diminuta (FU₀₀₉₀); for 48h;

DOI:10.3987/COM-06-10765

Reference yield:

(2RS,3SR)-(6-benzyloxy)hexane-2,3-diol → (4R,5S)-4-(3-benzyloxy)propyl-5-methyl-1,3-dioxolan-2-one (918819-00-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / pyridine / CH₂Cl₂ / -78 - 0 °C

2: 43 percent / Pseudomonas diminuta FU₀₀₉₀; polypeptone; yeast extract / glucose / aq. phosphate buffer / 48 h / 30 °C / pH 6.5

With pyridine; polypeptone; Pseudomonas diminuta FU₀₀₉₀; yeast extract; D-glucose; In phosphate buffer; dichloromethane;

DOI:10.1016/j.tet.2006.09.066

Reference yield:

(Z)-4-hexenol (928-91-6) → (4R,5S)-4-(3-benzyloxy)propyl-5-methyl-1,3-dioxolan-2-one (918819-00-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 3.7 g / NaH / tetrahydrofuran; various solvent(s) / 6 h / Heating

2: 3.9 g / 4-methylmorpholine N-oxide; OsO₄ / acetone; 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

3: 92 percent / pyridine / CH₂Cl₂ / -78 - 0 °C

4: 43 percent / Pseudomonas diminuta FU₀₀₉₀; polypeptone; yeast extract / glucose / aq. phosphate buffer / 48 h / 30 °C / pH 6.5

With pyridine; osmium(VIII) oxide; polypeptone; Pseudomonas diminuta FU₀₀₉₀; sodium hydride; 4-methylmorpholine N-oxide; yeast extract; D-glucose; In tetrahydrofuran; phosphate buffer; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1016/j.tet.2006.09.066

upstream raw materials:

(Z)-4-hexenol

benzyl bromide

(Z)-((hex-4-en-1-yloxy)methyl)benzene