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

Base Information

• Chemical Name: ((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-diphenyl-phosphane
• CAS No.: 115261-95-5
• Molecular Formula: C₂₆H₂₉O₃P
• Molecular Weight: 420.488
• Mol file: 115261-95-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about ((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-diphenyl-phosphane 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: 60.0%

(4S,5S)-p-toluolsulfonsaeure<(5-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>ester (78513-04-9) + sodium diphenylphosphide (4376-01-6) → ((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-diphenyl-phosphane (115261-95-5)

Guidance literature:

In tetrahydrofuran; 1,4-dioxane;

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

Reference yield:

2,3-O-isopropylidene-L-threitol (50622-09-8) → ((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-diphenyl-phosphane (115261-95-5)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride;

DOI:10.1248/cpb.41.1149

Reference yield:

benzyl bromide (100-39-0) → ((4R,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-diphenyl-phosphane (115261-95-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / NaH / tetrabutylammonium iodide / tetrahydrofuran

2: 98 percent / pyridine

3: 60 percent / dioxane; tetrahydrofuran

With pyridine; sodium hydride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; 1,4-dioxane;

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

upstream raw materials:

(4S,5S)-p-toluolsulfonsaeure<(5-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl)methyl>ester

sodium diphenylphosphide

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

2,3-O-isopropylidene-L-threitol

Downstream raw materials:

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

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

(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