methyl 2,3-dideoxy-5,6-O-isopropylidene-4-O-p-tolylsulfonyl-D-erythro-hexonate

Base Information

• Chemical Name: methyl 2,3-dideoxy-5,6-O-isopropylidene-4-O-p-tolylsulfonyl-D-erythro-hexonate
• CAS No.: 136963-32-1
• Molecular Formula: C₁₇H₂₄O₇S
• Molecular Weight: 372.439
• Mol file: 136963-32-1.mol

Synonyms:methyl 2,3-dideoxy-5,6-O-isopropylidene-4-O-p-tolylsulfonyl-D-erythro-hexonate

Chemical Property of methyl 2,3-dideoxy-5,6-O-isopropylidene-4-O-p-tolylsulfonyl-D-erythro-hexonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of methyl 2,3-dideoxy-5,6-O-isopropylidene-4-O-p-tolylsulfonyl-D-erythro-hexonate

There total 2 articles about methyl 2,3-dideoxy-5,6-O-isopropylidene-4-O-p-tolylsulfonyl-D-erythro-hexonate 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: 66.5%

methyl 2,3-dideoxy-5,6-O-isopropylidene-D-erythro-hexonate (127553-90-6) + p-toluenesulfonyl chloride (98-59-9) → methyl 2,3-dideoxy-5,6-O-isopropylidene-4-O-p-tolylsulfonyl-D-erythro-hexonate (136963-32-1)

Guidance literature:

With pyridine; at 5 ℃; for 48h;

DOI:10.1016/0008-6215(92)84152-I

Reference yield:

(S)-Chloro-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetic acid methyl ester (127529-99-1) → methyl 2,3-dideoxy-5,6-O-isopropylidene-4-O-p-tolylsulfonyl-D-erythro-hexonate (136963-32-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) NaOAc, 2) H₂ / 10percent Pd/C / 1) MeOH, reflux, overnight, 2) r.t., 1 atm, 4 h

2: 66.5 percent / pyridine / 48 h / 5 °C

With pyridine; hydrogen; sodium acetate; palladium on activated charcoal;

DOI:10.1016/0008-6215(92)84152-I

Reference yield: 79.5%

methyl 2,3-dideoxy-5,6-O-isopropylidene-4-O-p-tolylsulfonyl-D-erythro-hexonate (136963-32-1) → (4S,5R)-4,6-isopropylidenedioxy-4-p-toluenesulfonyloxyhexanal (136963-43-4)

Guidance literature:

With diisobutylaluminum hydride; In toluene; Petroleum ether; at -78 ℃; for 3h;

DOI:10.1016/0008-6215(92)84152-I

upstream raw materials:

methyl 2,3-dideoxy-5,6-O-isopropylidene-D-erythro-hexonate

p-toluenesulfonyl chloride

(S)-Chloro-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-acetic acid methyl ester

Downstream raw materials:

(4S,5R)-4,6-isopropylidenedioxy-4-p-toluenesulfonyloxyhexanal

Z-D-proline

(2R)-(+)-phenylmethyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate

(2R)-(+)-phenylmethyl 2-formylpyrrolidine-1-carboxylate

Refernces