p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside

Base Information

• Chemical Name: p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside
• CAS No.: 170156-80-6
• Molecular Formula: C₃₀H₃₄O₄
• Molecular Weight: 458.598
• Mol file: 170156-80-6.mol

Synonyms:p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside

Chemical Property of p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside

There total 4 articles about p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside 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:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + para-tert-butylphenol (98-54-4) → p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside (170156-80-6) + p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside (201232-72-6)

Guidance literature:

With FeCl₃/C; In dichloromethane; at 20 ℃; for 1.3h; Overall yield = 80percent;

DOI:10.1080/07328303.2020.1788575

Reference yield:

benzyl chloride (100-44-7) + (2R,3S,6R)-6-(4-tert-Butyl-phenoxy)-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol (201233-15-0) → p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside (170156-80-6)

Guidance literature:

With sodium hydroxide; In methanol; toluene; at 60 ℃; for 5h; Yield given;

DOI:10.1080/00397919508011424

Reference yield:

4-t-butylphenyl4, 6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside (171082-23-8) → p-tert-butylphenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside (170156-80-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol / 24 h / 25 °C

2: aq. NaOH / methanol; toluene / 5 h / 60 °C

With sodium hydroxide; sodium methylate; In methanol; toluene;

DOI:10.1080/00397919508011424

upstream raw materials:

benzyl chloride

(2R,3S,6R)-6-(4-tert-Butyl-phenoxy)-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol

4-t-butylphenyl4, 6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside

D-glucal triacetate

Downstream raw materials:

3-(4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-1-propene

ethyl 2(R,S)-amino-2-(4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)acetate