(3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal

Base Information

• Chemical Name: (3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal
• CAS No.: 103795-36-4
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321
• Mol file: 103795-36-4.mol

Synonyms:(3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal

Chemical Property of (3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal

There total 33 articles about (3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal 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: 97.0%

3-O-benzyl-2-deoxy-4,5-O-isopropylidene-D-erythro-pentose dipropyl mercaptal (111717-54-5) → (3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal (103795-36-4)

Guidance literature:

With mercury dichloride; mercury(II) oxide; In water; acetonitrile; at 0 ℃; for 0.5h;

DOI:10.1021/jo00239a028

Reference yield: 86.0%

(2S,3R)-2-<2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybut-1-yl>-1,3-dithiane (128161-77-3) → (3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal (103795-36-4)

Guidance literature:

With water; calcium carbonate; methyl iodide; In acetonitrile; at 40 ℃; for 17h;

DOI:10.1021/jo00301a035

Reference yield:

(R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane (87604-53-3) → (3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal (103795-36-4)

Guidance literature:

With ozone; triphenylphosphine; Yield given. Multistep reaction; 1.) methanol, -78 deg C, 2.) methanol, 12 h;

upstream raw materials:

(2S,3R)-2-<2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybut-1-yl>-1,3-dithiane

(R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane

2-[(S)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-thiazole

E-(2R,3S,5ξ,8ξ)-3-O-benzyl-1,2-O-isopropylidene-6-nonen-1,2,3,5,8-pentaol

Downstream raw materials:

Acetic acid (E)-(7S,8R)-7-benzyloxy-8,9-dihydroxy-non-4-enyl ester

(E)-(S)-7-Benzyloxy-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid ethyl ester

C₂₄H₂₆O₆

(E)-(2R,5R,6S)-6-Benzyloxy-3,13,20-trioxa-tricyclo[13.2.2.1^2,5]icosa-1⁽¹⁸⁾,8,15⁽¹⁹⁾,16-tetraen-14-one