(2S,3S)-4-dibenzylamino-2,3-O-isopropylidenebutane-1,2,3-triol

Base Information

• Chemical Name: (2S,3S)-4-dibenzylamino-2,3-O-isopropylidenebutane-1,2,3-triol
• CAS No.: 260273-04-9
• Molecular Formula: C₂₁H₂₇NO₃
• Molecular Weight: 341.45
• Mol file: 260273-04-9.mol

Synonyms:(2S,3S)-4-dibenzylamino-2,3-O-isopropylidenebutane-1,2,3-triol

Chemical Property of (2S,3S)-4-dibenzylamino-2,3-O-isopropylidenebutane-1,2,3-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-4-dibenzylamino-2,3-O-isopropylidenebutane-1,2,3-triol

There total 3 articles about (2S,3S)-4-dibenzylamino-2,3-O-isopropylidenebutane-1,2,3-triol 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: 85.0%

benzyl bromide (100-39-0) + (2S,3S)-4-amino-2,3-O-isopropylidenebutane-1,2,3-triol (84252-36-8) → (2S,3S)-4-dibenzylamino-2,3-O-isopropylidenebutane-1,2,3-triol (260273-04-9)

Guidance literature:

With potassium carbonate; In acetonitrile; for 24.5h; Heating;

DOI:10.1002/(SICI)1099-0682(200002)2000:2<351::AID-EJIC351>3.0.CO;2-Q

Reference yield:

(4S,5S)-4-hydroxymethyl-2,2-dimethyl-5-tosyloxymethyl-1,3-dioxolane (70831-49-1,73711-65-6,58789-44-9) → (2S,3S)-4-dibenzylamino-2,3-O-isopropylidenebutane-1,2,3-triol (260273-04-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / NaN₃ / dimethylformamide / 24 h / Heating

2: 100 percent / H₂ / Pd/C / ethanol / 48 h / 20 °C

3: 85 percent / K₂CO₃ / acetonitrile / 24.5 h / Heating

With sodium azide; hydrogen; potassium carbonate; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide; acetonitrile; 1: Substitution / 2: Catalytic hydrogenation / 3: Dehydrobromination;

DOI:10.1002/(SICI)1099-0682(200002)2000:2<351::AID-EJIC351>3.0.CO;2-Q

Reference yield:

((4S,5S)-5-(azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol (84252-35-7) → (2S,3S)-4-dibenzylamino-2,3-O-isopropylidenebutane-1,2,3-triol (260273-04-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / Pd/C / ethanol / 48 h / 20 °C

2: 85 percent / K₂CO₃ / acetonitrile / 24.5 h / Heating

With hydrogen; potassium carbonate; palladium on activated charcoal; In ethanol; acetonitrile; 1: Catalytic hydrogenation / 2: Dehydrobromination;

DOI:10.1002/(SICI)1099-0682(200002)2000:2<351::AID-EJIC351>3.0.CO;2-Q

upstream raw materials:

benzyl bromide

(2S,3S)-4-amino-2,3-O-isopropylidenebutane-1,2,3-triol

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

((4S,5S)-5-(azidomethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methanol

Downstream raw materials:

(2R,3S)-4-dibenzylamino-2,3-O-isopropylidene-1-O-tosylbutane-1,2,3-triol

(2R,3S)-4-dibenzylamino-1-diphenylphosphanyl-2,3-O-isopropylidenebutane-2,3-diol