Toluene-4-sulfonic acid 2-((4S,5R)-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid 2-((4S,5R)-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl ester
• CAS No.: 220317-67-9
• Molecular Formula: C₂₀H₃₁NO₇S
• Molecular Weight: 429.535
• Mol file: 220317-67-9.mol

Synonyms:Toluene-4-sulfonic acid 2-((4S,5R)-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl ester

Chemical Property of Toluene-4-sulfonic acid 2-((4S,5R)-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid 2-((4S,5R)-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl ester

There total 5 articles about Toluene-4-sulfonic acid 2-((4S,5R)-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl ester 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: 95.0%

p-toluenesulfonyl chloride (98-59-9) + [(4S,5R)-4-(2-Hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxan-5-yl]-carbamic acid tert-butyl ester (220317-66-8) → Toluene-4-sulfonic acid 2-((4S,5R)-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl ester (220317-67-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 1.5h; Ambient temperature;

DOI:10.1039/a805998e

Reference yield:

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine (95715-87-0) → Toluene-4-sulfonic acid 2-((4S,5R)-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl ester (220317-67-9)

Guidance literature:

Multi-step reaction with 5 steps

1: CrCl₂ / tetrahydrofuran / 2.5 h / Ambient temperature

2: p-TsOH*H₂O / methanol / 2 h / Ambient temperature

3: p-TsOH*H₂O / 2 h / Ambient temperature

4: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, -78 deg C, 2.) MeOH, -78 deg C

5: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / Ambient temperature

With chromium dichloride; dmap; sodium tetrahydroborate; toluene-4-sulfonic acid; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1039/a805998e

Reference yield:

((1R)-2-hydroxy-1-hydroxymethylpent-4-enyl)carbamic acid tert-butyl ester (220317-63-5) → Toluene-4-sulfonic acid 2-((4S,5R)-5-tert-butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-ethyl ester (220317-67-9)

Guidance literature:

Multi-step reaction with 3 steps

1: p-TsOH*H₂O / 2 h / Ambient temperature

2: 1.) O₃, 2.) NaBH₄ / 1.) MeOH, -78 deg C, 2.) MeOH, -78 deg C

3: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / Ambient temperature

With dmap; sodium tetrahydroborate; toluene-4-sulfonic acid; ozone; triethylamine; In dichloromethane;

DOI:10.1039/a805998e

upstream raw materials:

p-toluenesulfonyl chloride

[(4S,5R)-4-(2-Hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxan-5-yl]-carbamic acid tert-butyl ester

(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine

((1R)-2-hydroxy-1-hydroxymethylpent-4-enyl)carbamic acid tert-butyl ester

Downstream raw materials:

(2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidinium hydrochloride