(1S)-1-methoxymethoxyvitamin D₃

Base Information

• Chemical Name: (1S)-1-methoxymethoxyvitamin D₃
• CAS No.: 101046-92-8
• Molecular Formula: C₂₉H₄₈O₃
• Molecular Weight: 444.698
• Mol file: 101046-92-8.mol

Synonyms:(1S)-1-methoxymethoxyvitamin D₃

Chemical Property of (1S)-1-methoxymethoxyvitamin D₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S)-1-methoxymethoxyvitamin D₃

There total 11 articles about (1S)-1-methoxymethoxyvitamin D₃ 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: 77.0%

(1S)-3-deoxy-6-hydroxy-1-methoxymethoxy-3,5-cyclo-5,6-dihydrovitamin D3 (101046-91-7,101054-33-5,111687-66-2) → (1S)-1-methoxymethoxyvitamin D3 (101046-92-8)

Guidance literature:

With water; toluene-4-sulfonic acid; In 1,4-dioxane; at 55 ℃; for 0.0833333h;

Reference yield: 51.0%

(1S,6R)-3-deoxy-6-methoxy-1-methoxymethoxy-3,5-cyclo-5,6-dihydrovitamin D3 (101046-93-9) → (1S)-1-methoxymethoxyvitamin D3 (101046-92-8)

Guidance literature:

With water; toluene-4-sulfonic acid; In 1,4-dioxane; at 55 ℃; for 0.0833333h;

Reference yield:

(-)-menthyl (1R,5R)-2-methylenebicyclo<3.1.0>hexane-1-carboxylate (93489-96-4) → (1S)-1-methoxymethoxyvitamin D3 (101046-92-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 37 percent / SeO₂, tBuOOH / CH₂Cl₂ / 1 h / Ambient temperature

2: 80 percent / Hunig base / 10 h / Ambient temperature

3: 92 percent / LiAlH₄ / tetrahydrofuran / 1 h / Ambient temperature

4: 76 percent / PCC / CH₂Cl₂ / 2 h / Ambient temperature

5: 34 percent / t-BuLi / tetrahydrofuran / 1 h / -78 °C

6: 77 percent / pTsOH / H₂O; dioxane / 0.08 h / 55 °C

With tert.-butylhydroperoxide; lithium aluminium tetrahydride; selenium(IV) oxide; tert.-butyl lithium; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

DOI:10.1246/cl.1985.1131

upstream raw materials:

(1S)-3-deoxy-6-hydroxy-1-methoxymethoxy-3,5-cyclo-5,6-dihydrovitamin D₃

(1S,6R)-3-deoxy-6-methoxy-1-methoxymethoxy-3,5-cyclo-5,6-dihydrovitamin D₃

8-bromomethylenedes-AB-cholestane

(-)-menthyl (1R,5R)-2-methylenebicyclo<3.1.0>hexane-1-carboxylate

Downstream raw materials:

1α-hydroxyvitamin D3

Refernces

• 1、 Nemoto, Hideo,Kimura, Toshihiko,Kurobe, Hiroshi,Fukumoto, Keiichiro,Kametani, Tetsuji. "A STEREOSELECTIVE SYNTHESIS OF 1 α-HYDROXY-VITAMIN D3". . p. 1131 - 1132. Retrieved 2007/10/02.