(4S,5S)-4-[(benzyloxy)methyl]-2,2,5-trimethyl-1,3-dioxan-5-ol

Base Information

• Chemical Name: (4S,5S)-4-[(benzyloxy)methyl]-2,2,5-trimethyl-1,3-dioxan-5-ol
• CAS No.: 943329-64-4
• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.337
• Mol file: 943329-64-4.mol

Synonyms:(4S,5S)-4-[(benzyloxy)methyl]-2,2,5-trimethyl-1,3-dioxan-5-ol

Chemical Property of (4S,5S)-4-[(benzyloxy)methyl]-2,2,5-trimethyl-1,3-dioxan-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-[(benzyloxy)methyl]-2,2,5-trimethyl-1,3-dioxan-5-ol

There total 3 articles about (4S,5S)-4-[(benzyloxy)methyl]-2,2,5-trimethyl-1,3-dioxan-5-ol 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%

methyllithium (917-54-4) + (4S)-4-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-one (126177-95-5) → (4S,5S)-4-[(benzyloxy)methyl]-2,2,5-trimethyl-1,3-dioxan-5-ol (943329-64-4) + (4S,5R)-4-[(benzyloxy)methyl]-2,2,5-trimethyl-1,3-dioxan-5-ol

Guidance literature:

In tetrahydrofuran; diethyl ether; at -90 ℃; for 3h;

DOI:10.1055/s-2007-965967

Reference yield:

C20H30N2O4 → (4S,5S)-4-[(benzyloxy)methyl]-2,2,5-trimethyl-1,3-dioxan-5-ol (943329-64-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.64 g / aq. oxalic acid / diethyl ether / 2 h / 20 °C

2: 75 percent / tetrahydrofuran; diethyl ether / 3 h / -90 °C

With oxalic acid; In tetrahydrofuran; diethyl ether;

DOI:10.1055/s-2007-965967

Reference yield:

(S)-(+)-1-(2,2-dimethyl-1,3-dioxan-5-ylidenamino)-2-methoxymethylpyrrolidine (126178-07-2) → (4S,5S)-4-[(benzyloxy)methyl]-2,2,5-trimethyl-1,3-dioxan-5-ol (943329-64-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tert-butyllithium / tetrahydrofuran; pentane / 2 h / -78 °C

1.2: tetrahydrofuran; pentane / -100 - 20 °C

2.1: 0.64 g / aq. oxalic acid / diethyl ether / 2 h / 20 °C

3.1: 75 percent / tetrahydrofuran; diethyl ether / 3 h / -90 °C

With tert.-butyl lithium; oxalic acid; In tetrahydrofuran; diethyl ether; pentane;

DOI:10.1055/s-2007-965967

upstream raw materials:

methyllithium

(4S)-4-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-one

(S)-(+)-1-(2,2-dimethyl-1,3-dioxan-5-ylidenamino)-2-methoxymethylpyrrolidine

Downstream raw materials:

(2S,3S)-4-(benzyloxy)-2-methylbutane-1,2,3-triol

(2S,3S)-2-methylbutane-1,2,3,4-tetraol