(2R,3S,4S)-2,3,5-tri(benzyloxy)-1,4-di(methylsulfonyloxy)pentane

Base Information

• Chemical Name: (2R,3S,4S)-2,3,5-tri(benzyloxy)-1,4-di(methylsulfonyloxy)pentane
• CAS No.: 135910-18-8
• Molecular Formula: C₂₈H₃₄O₉S₂
• Molecular Weight: 578.705
• Mol file: 135910-18-8.mol

Synonyms:(2R,3S,4S)-2,3,5-tri(benzyloxy)-1,4-di(methylsulfonyloxy)pentane

Chemical Property of (2R,3S,4S)-2,3,5-tri(benzyloxy)-1,4-di(methylsulfonyloxy)pentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-2,3,5-tri(benzyloxy)-1,4-di(methylsulfonyloxy)pentane

There total 5 articles about (2R,3S,4S)-2,3,5-tri(benzyloxy)-1,4-di(methylsulfonyloxy)pentane 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:

2,3,5-tri-O-benzyl-L-xylofuranose (16838-89-4,17073-88-0,60933-68-8,60933-69-9,73068-66-3,89361-52-4,89615-42-9,89615-45-2,96192-07-3) → (2R,3S,4S)-2,3,5-tri(benzyloxy)-1,4-di(methylsulfonyloxy)pentane (135910-18-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / ethanol / 0 - 20 °C

2: pyridine / 0 - 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; In ethanol;

DOI:10.1021/acs.orglett.5b02029

Reference yield:

(3R,4R,5S)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene (137820-47-4) → (2R,3S,4S)-2,3,5-tri(benzyloxy)-1,4-di(methylsulfonyloxy)pentane (135910-18-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dimethylsulfide borane complex / tetrahydrofuran / 0 - 20 °C

1.2: 3 h / 0 - 20 °C

2.1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C

With dmap; dimethylsulfide borane complex; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1055/s-0035-1562438

Reference yield:

L-xylose (41546-31-0) → (2R,3S,4S)-2,3,5-tri(benzyloxy)-1,4-di(methylsulfonyloxy)pentane (135910-18-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: acetyl chloride / 2 h / 0 - 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 12 h / 0 - 20 °C

3.1: trifluoroacetic acid / water; acetonitrile / 4 h / 80 °C

4.1: n-butyllithium / tetrahydrofuran; cyclohexane / -20 °C / Inert atmosphere

4.2: -20 - 20 °C

5.1: dimethylsulfide borane complex / tetrahydrofuran / 0 - 20 °C

5.2: 3 h / 0 - 20 °C

6.1: triethylamine; dmap / dichloromethane / 2 h / 0 - 20 °C

With dmap; n-butyllithium; dimethylsulfide borane complex; sodium hydride; triethylamine; acetyl chloride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; acetonitrile; 4.1: |Wittig Olefination / 4.2: |Wittig Olefination;

DOI:10.1055/s-0035-1562438

upstream raw materials:

2,3,5-tri-O-benzyl-L-xylofuranose

(3R,4R,5S)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene

L-xylose

(2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol

Downstream raw materials:

1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-arabinitol

2-(2R,3R,4R)-3,4-bis(benzyloxy)-2-[(benzyloxy)methyl]-1-[(2-hydroxy)ethyl]-1H-pyrrolidine

(2R,3R,4R)-3,4-bis(benzyloxy)-2-benzyloxymethyl-N-hydroxypyrrolidine

2,3,5-tri-O-benzyl-1,4-benzylimino-1,4-dideoxy-D-arabinitol