(4S,5R)-5-(dicyclohexylphosphino)methyl-4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane

Base Information

• Chemical Name: (4S,5R)-5-(dicyclohexylphosphino)methyl-4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane
• CAS No.: 115261-97-7
• Molecular Formula: C₁₉H₃₅O₄P
• Molecular Weight: 358.458
• Mol file: 115261-97-7.mol

Synonyms:(4S,5R)-5-(dicyclohexylphosphino)methyl-4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane

Chemical Property of (4S,5R)-5-(dicyclohexylphosphino)methyl-4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-5-(dicyclohexylphosphino)methyl-4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane

There total 6 articles about (4S,5R)-5-(dicyclohexylphosphino)methyl-4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane 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: 75.0%

(4S,5R)-4-(benzyloxy)methyl-5-(diphenylphosphinyl)methyl-2,2-dimethyl-1,3-dioxolane (115261-96-6) → (4S,5R)-5-(dicyclohexylphosphino)methyl-4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane (115261-97-7)

Guidance literature:

With hydrogen; Raney Ni (W-6); In ethanol; at 70 ℃; for 24h;

DOI:10.1016/S0040-4039(00)96352-4

Reference yield:

(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane (78469-77-9,81076-11-1,128820-40-6,78513-03-8) → (4S,5R)-5-(dicyclohexylphosphino)methyl-4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane (115261-97-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / pyridine / -30 °C

2: 1.) Na / 1.) 1,4-dioxane, reflux, 3 h, 2.) 1,4-dioxane, THF, a) O deg C, 2 h, b) RT, overnight

3: 10percent aq. H₂O₂ / methanol / 0.5 h / 0 °C

4: 75 percent / H₂ / Raney Ni / ethanol / 20 h / 70 °C / 53200 Torr

With pyridine; hydrogen; dihydrogen peroxide; sodium; nickel; In methanol; ethanol;

DOI:10.1248/cpb.41.1149

Reference yield:

2,3-O-isopropylidene-L-threitol (50622-09-8) → (4S,5R)-5-(dicyclohexylphosphino)methyl-4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane (115261-97-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, reflux, 1 h, 2.) THF, RT, overnight

2: 98 percent / pyridine / -30 °C

3: 1.) Na / 1.) 1,4-dioxane, reflux, 3 h, 2.) 1,4-dioxane, THF, a) O deg C, 2 h, b) RT, overnight

4: 10percent aq. H₂O₂ / methanol / 0.5 h / 0 °C

5: 75 percent / H₂ / Raney Ni / ethanol / 20 h / 70 °C / 53200 Torr

With pyridine; hydrogen; dihydrogen peroxide; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; nickel; In methanol; ethanol;

DOI:10.1248/cpb.41.1149

upstream raw materials:

(4S,5R)-4-(benzyloxy)methyl-5-(diphenylphosphinyl)methyl-2,2-dimethyl-1,3-dioxolane

(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane

2,3-O-isopropylidene-L-threitol

((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-diphenyl-phosphane

Downstream raw materials:

(4S,5R)-5-(dicyclohexylphosphinyl)methyl-2,2-dimethyl-4-(methylsulfonyloxy)methyl-1,3-dioxolane

(4R,5R)-4-(dicyclohexylphosphinyl)methyl-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane

<(4R,5R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl(dicyclohexyl)-5-ylmethyl(diphenyl)>bisphosphine