[(4R,6R)-6-(Cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid

Base Information

• Chemical Name: [(4R,6R)-6-(Cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid
• CAS No.: 807312-27-2
• Molecular Formula: C₁₀H₁₅NO₄
• Molecular Weight: 213.233
• DSSTox Substance ID: DTXSID70450472
• Nikkaji Number: J1.689.875I
• Wikidata: Q82270216
• Mol file: 807312-27-2.mol

Synonyms:807312-27-2;[(4R,6R)-6-(Cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid;2-[(4R,6R)-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid;(4R,6R)-6-(Cyanomethyl)-2,2-dimethyl-1,3-Dioxane-4-acetic acid;SCHEMBL2476599;DTXSID70450472;GODYJJJBRGLOET-HTQZYQBOSA-N;(+/-)-cis-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid;(+/-)-cis-6-(cyanomethyl)-2,2-dimethyl-1,3-dioxane4-acetic acid;(4R)-2,2-Dimethyl-6beta-(cyanomethyl)-1,3-dioxane-4beta-acetic acid

Chemical Property of [(4R,6R)-6-(Cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid

Chemical Property:

• PSA: 79.55000
• LogP: 1.28498
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 213.10010796
• Heavy Atom Count: 15
• Complexity: 291

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC(CC(O1)CC(=O)O)CC#N)C
• Isomeric SMILES: CC1(O[C@@H](C[C@@H](O1)CC(=O)O)CC#N)C

Technology Process of [(4R,6R)-6-(Cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid

There total 7 articles about [(4R,6R)-6-(Cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl]acetic acid 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: 70.0%

[(4S,6S)-2,2-Dimethyl-6-(2-oxo-ethyl)-[1,3]dioxan-4-yl]-acetonitrile → (6-cyanomethyl-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid (807312-27-2)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In acetone; at 0 ℃;

DOI:10.1016/S0040-4039(02)00175-2

Reference yield:

1, 6-heptadien-4-ol (2883-45-6) → (6-cyanomethyl-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid (807312-27-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: BuLi / tetrahydrofuran

1.3: 91 percent / I₂

2.1: 90 percent / p-toluenesulfonic acid / acetone / 20 °C

3.1: 80 percent / dimethylsulfoxide / 125 h / 40 °C

4.1: 65 percent / OsO₄; NaIO₄ / dioxane; H₂O

5.1: 70 percent / CrO₃; H₂SO₄ / acetone / 0 °C

With chromium(VI) oxide; sodium periodate; osmium(VIII) oxide; n-butyllithium; sulfuric acid; toluene-4-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; water; dimethyl sulfoxide; acetone;

DOI:10.1016/S0040-4039(02)00175-2

Reference yield:

(+/-)-(4S,6S)-4-allyl-6-(iodomethyl)-1,3-dioxan-2-one → (6-cyanomethyl-2,2-dimethyl-1,3-dioxan-4-yl)acetic acid (807312-27-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / p-toluenesulfonic acid / acetone / 20 °C

2: 80 percent / dimethylsulfoxide / 125 h / 40 °C

3: 65 percent / OsO₄; NaIO₄ / dioxane; H₂O

4: 70 percent / CrO₃; H₂SO₄ / acetone / 0 °C

With chromium(VI) oxide; sodium periodate; osmium(VIII) oxide; sulfuric acid; toluene-4-sulfonic acid; In 1,4-dioxane; water; dimethyl sulfoxide; acetone;

DOI:10.1016/S0040-4039(02)00175-2

upstream raw materials:

1, 6-heptadien-4-ol