2,3-Bis(p-methoxybenzyl)-1,1-bis(ethylthio)-4,5-isopropylidene-D-arabinose

Base Information

• Chemical Name: 2,3-Bis(p-methoxybenzyl)-1,1-bis(ethylthio)-4,5-isopropylidene-D-arabinose
• CAS No.: 153098-16-9
• Molecular Formula: C₂₈H₄₀O₆S₂
• Molecular Weight: 536.754
• Mol file: 153098-16-9.mol

Synonyms:2,3-Bis(p-methoxybenzyl)-1,1-bis(ethylthio)-4,5-isopropylidene-D-arabinose

Chemical Property of 2,3-Bis(p-methoxybenzyl)-1,1-bis(ethylthio)-4,5-isopropylidene-D-arabinose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-Bis(p-methoxybenzyl)-1,1-bis(ethylthio)-4,5-isopropylidene-D-arabinose

There total 1 articles about 2,3-Bis(p-methoxybenzyl)-1,1-bis(ethylthio)-4,5-isopropylidene-D-arabinose 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: 76.0%

p-methoxybenzyl chloride (824-94-2) + 4,5-O-isopropylidene-D-arabinose diethyldithioacetal (70337-25-6) → 2,3-Bis(p-methoxybenzyl)-1,1-bis(ethylthio)-4,5-isopropylidene-D-arabinose (153098-16-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 25 ℃; for 4h;

DOI:10.1021/jo00079a033

Reference yield:

2,3-Bis(p-methoxybenzyl)-1,1-bis(ethylthio)-4,5-isopropylidene-D-arabinose (153098-16-9) → (E)-(4S,5R)-5-(S)-Aziridin-2-yl-2-benzoylamino-3-bromo-4,5-bis-(4-methoxy-benzyloxy)-pent-2-enoic acid ethyl ester (139427-63-7)

Guidance literature:

Multi-step reaction with 13 steps

1: NBS, 2,6-lutidine, H₂O / acetonitrile

2: NaBH₄ / ethanol / 2 h / 25 °C

3: 95 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

4: 66 percent / pyridinium p-toluenesulfonate / methanol / 56 h / 50 °C

5: pyridine / CH₂Cl₂ / 0 °C

6: NaN₃ / dimethylformamide / 8 h / 50 °C

7: 76 percent / Ph₃P / toluene / 0.5 h / 40 °C

8: 64 percent / pyridine / CH₂Cl₂ / 0.25 h

9: 92 percent / TBAF / tetrahydrofuran / 8 h / Ambient temperature

10: DMSO, oxalyl chloride / CH₂Cl₂ / 0.17 h / -78 °C

11: LDA / heptane; tetrahydrofuran / 1.) -78 deg C, 30 min; 0 deg C, 1 h, 2.) -20 deg C, overnight

12: Br₂, 2,6-lutidine / CH₂Cl₂ / 1.5 h / -10 °C

13: trichloroacetic acid / CD₃CN / 0.75 h / Ambient temperature

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; oxalyl dichloride; tetrabutyl ammonium fluoride; water; bromine; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triphenylphosphine; lithium diisopropyl amide; trichloroacetic acid; In tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane; [D₃]acetonitrile; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo00079a033

Reference yield:

2,3-Bis(p-methoxybenzyl)-1,1-bis(ethylthio)-4,5-isopropylidene-D-arabinose (153098-16-9) → Ethyl (E)-2-(N-benzoylamino)-3-bromo-4(S),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate (139427-61-5)

Guidance literature:

Multi-step reaction with 12 steps

1: NBS, 2,6-lutidine, H₂O / acetonitrile

2: NaBH₄ / ethanol / 2 h / 25 °C

3: 95 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

4: 66 percent / pyridinium p-toluenesulfonate / methanol / 56 h / 50 °C

5: pyridine / CH₂Cl₂ / 0 °C

6: NaN₃ / dimethylformamide / 8 h / 50 °C

7: 76 percent / Ph₃P / toluene / 0.5 h / 40 °C

8: 64 percent / pyridine / CH₂Cl₂ / 0.25 h

9: 92 percent / TBAF / tetrahydrofuran / 8 h / Ambient temperature

10: DMSO, oxalyl chloride / CH₂Cl₂ / 0.17 h / -78 °C

11: LDA / heptane; tetrahydrofuran / 1.) -78 deg C, 30 min; 0 deg C, 1 h, 2.) -20 deg C, overnight

12: Br₂, 2,6-lutidine / CH₂Cl₂ / 1.5 h / -10 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; oxalyl dichloride; tetrabutyl ammonium fluoride; water; bromine; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; n-heptane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo00079a033

upstream raw materials:

p-methoxybenzyl chloride

4,5-O-isopropylidene-D-arabinose diethyldithioacetal

Downstream raw materials:

(2S,3R)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,3-bis-(4-methoxy-benzyloxy)-propionaldehyde

(E)-(4S,5R)-5-(S)-Aziridin-2-yl-2-benzoylamino-3-bromo-4,5-bis-(4-methoxy-benzyloxy)-pent-2-enoic acid ethyl ester

(2'S)-3--2(R),3(R)-bis<(p-methoxybenzyl)oxy>-1-propanal

Ethyl (E)-2-(N-Benzoylamino)-4(R),5(R)-bis<(p-methoxybenzyl)oxy>-5--2-pentenoate