(1S,2S)-3-(benzyloxy)-1-((S)-2,2-dimethyl-5-oxo-1,3-dioxan-4-yl)-1-hydroxypropan-2-yl acetate

Base Information

• Chemical Name: (1S,2S)-3-(benzyloxy)-1-((S)-2,2-dimethyl-5-oxo-1,3-dioxan-4-yl)-1-hydroxypropan-2-yl acetate
• CAS No.: 1459197-97-7
• Molecular Formula: C₁₈H₂₄O₇
• Molecular Weight: 352.384
• Mol file: 1459197-97-7.mol

Synonyms:(1S,2S)-3-(benzyloxy)-1-((S)-2,2-dimethyl-5-oxo-1,3-dioxan-4-yl)-1-hydroxypropan-2-yl acetate

Chemical Property of (1S,2S)-3-(benzyloxy)-1-((S)-2,2-dimethyl-5-oxo-1,3-dioxan-4-yl)-1-hydroxypropan-2-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S)-3-(benzyloxy)-1-((S)-2,2-dimethyl-5-oxo-1,3-dioxan-4-yl)-1-hydroxypropan-2-yl acetate

There total 3 articles about (1S,2S)-3-(benzyloxy)-1-((S)-2,2-dimethyl-5-oxo-1,3-dioxan-4-yl)-1-hydroxypropan-2-yl acetate 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%

2,2,-dimethyl-1,3-dioxan-5-one (74181-34-3) + 2-O-acetyl-3-O-benzyl-L-glyceraldehyde (104863-51-6) → (1S,2S)-3-(benzyloxy)-1-((S)-2,2-dimethyl-5-oxo-1,3-dioxan-4-yl)-1-hydroxypropan-2-yl acetate (1459197-97-7)

Guidance literature:

With L-proline; stereoselective reaction;

DOI:10.1016/j.tetasy.2016.12.011

Reference yield:

5-O-acetyl-6-O-benzyl-2,3-O-isopropylidene-L-gulono-γ-lactone (1459197-95-5) → (1S,2S)-3-(benzyloxy)-1-((S)-2,2-dimethyl-5-oxo-1,3-dioxan-4-yl)-1-hydroxypropan-2-yl acetate (1459197-97-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: copper(II) choride dihydrate / acetonitrile / 2 h / Inert atmosphere; Reflux

2.1: sodium periodate; sodium hydrogencarbonate / water / 4 h / 0 °C / pH 5.5 / Inert atmosphere

3.1: L-proline / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

3.2: 144 h / 5 °C / Inert atmosphere

With sodium periodate; copper(II) choride dihydrate; sodium hydrogencarbonate; L-proline; In water; N,N-dimethyl-formamide; acetonitrile; 3.1: |Aldol Addition / 3.2: |Aldol Addition;

DOI:10.1016/j.tetlet.2013.08.108

Reference yield:

6-O-benzyl-2,3-O-isopropylidene-L-gulono-γ-lactone (1459197-94-4) → (1S,2S)-3-(benzyloxy)-1-((S)-2,2-dimethyl-5-oxo-1,3-dioxan-4-yl)-1-hydroxypropan-2-yl acetate (1459197-97-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap; triethylamine / dichloromethane / 6.5 h / 20 °C / Inert atmosphere

2.1: copper(II) choride dihydrate / acetonitrile / 2 h / Inert atmosphere; Reflux

3.1: sodium periodate; sodium hydrogencarbonate / water / 4 h / 0 °C / pH 5.5 / Inert atmosphere

4.1: L-proline / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

4.2: 144 h / 5 °C / Inert atmosphere

With dmap; sodium periodate; copper(II) choride dihydrate; sodium hydrogencarbonate; triethylamine; L-proline; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 4.1: |Aldol Addition / 4.2: |Aldol Addition;

DOI:10.1016/j.tetlet.2013.08.108

upstream raw materials:

6-O-benzyl-2,3-O-isopropylidene-L-gulono-γ-lactone

5-O-acetyl-6-O-benzyl-2,3-O-isopropylidene-L-gulono-γ-lactone

2,2,-dimethyl-1,3-dioxan-5-one

2-O-acetyl-3-O-benzyl-L-glyceraldehyde

Downstream raw materials:

(3S,4S,5S)-1,3,4,5,6-pentahydroxyhexan-2-one