(2S,3R,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxyethyl)-3-mesyloxypyrrolidine

Base Information

• Chemical Name: (2S,3R,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxyethyl)-3-mesyloxypyrrolidine
• CAS No.: 174193-32-9
• Molecular Formula: C₂₁H₂₇NO₉S₃
• Molecular Weight: 533.645

Synonyms:(2S,3R,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxyethyl)-3-mesyloxypyrrolidine

Chemical Property of (2S,3R,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxyethyl)-3-mesyloxypyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (2S,3R,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxyethyl)-3-mesyloxypyrrolidine

There total 9 articles about (2S,3R,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxyethyl)-3-mesyloxypyrrolidine 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: 91.0%

p-toluenesulfonyl chloride (98-59-9) + (2S,3R,2'R)-N-tosyl-2-(1',2'-dihydroxyethyl)-3-mesyloxypyrrolidine (174193-31-8) → (2S,3R,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxyethyl)-3-mesyloxypyrrolidine (174193-32-9)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(96)01049-6

Reference yield:

divinylcarbinol (922-65-6) → (2S,3R,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxyethyl)-3-mesyloxypyrrolidine (174193-32-9)

Guidance literature:

Multi-step reaction with 10 steps

1: L-(+)-DIPT, TBHP, Ti(OiPr)4, molecular sieves 4 Angstroem / CH₂Cl₂ / 240 h / -20 °C

2: acetone; diethyl ether / 15 h / Ambient temperature

3: 98 percent / p-TSA / CH₂Cl₂ / Ambient temperature

4: LAH / diethyl ether / 1.5 h / Ambient temperature

5: Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 91 percent / p-TSA, HCl / methanol; H₂O / 0.5 h / Ambient temperature

7: 98 percent / pyridine / CH₂Cl₂ / 2 h / Ambient temperature

8: 100 percent / KOH / H₂O; acetone / Ambient temperature

9: 81 percent / OsO₄, K₃Fe(CN)6, K₂CO₃, (DHQD)2PHAL / 2-methyl-propan-2-ol; H₂O / 48 h / Ambient temperature

10: 91 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; potassium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; L-(+)-diisopropyl tartrate; 4 A molecular sieve; potassium carbonate; toluene-4-sulfonic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; potassium hexacyanoferrate(III); In methanol; diethyl ether; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1016/S0040-4020(96)01049-6

Reference yield:

(S)-1-[(R)-oxiran-2-yl]prop-2-enol (100017-22-9) → (2S,3R,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxyethyl)-3-mesyloxypyrrolidine (174193-32-9)

Guidance literature:

Multi-step reaction with 9 steps

1: acetone; diethyl ether / 15 h / Ambient temperature

2: 98 percent / p-TSA / CH₂Cl₂ / Ambient temperature

3: LAH / diethyl ether / 1.5 h / Ambient temperature

4: Et₃N / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 91 percent / p-TSA, HCl / methanol; H₂O / 0.5 h / Ambient temperature

6: 98 percent / pyridine / CH₂Cl₂ / 2 h / Ambient temperature

7: 100 percent / KOH / H₂O; acetone / Ambient temperature

8: 81 percent / OsO₄, K₃Fe(CN)6, K₂CO₃, (DHQD)2PHAL / 2-methyl-propan-2-ol; H₂O / 48 h / Ambient temperature

9: 91 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; hydrogenchloride; potassium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; potassium carbonate; toluene-4-sulfonic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; potassium hexacyanoferrate(III); In methanol; diethyl ether; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1016/S0040-4020(96)01049-6

upstream raw materials:

p-toluenesulfonyl chloride

(2S,3R,2'R)-N-tosyl-2-(1',2'-dihydroxyethyl)-3-mesyloxypyrrolidine

divinylcarbinol

(S)-1-[(R)-oxiran-2-yl]prop-2-enol

Downstream raw materials:

(1S,4S,5R)-N-tosyl-4-hydroxy-2,6-diazabicyclo<3,3,0>octane

(1S,4S,5R)-N²-benzyl-N⁶-tosyl-4-hydroxy-2,6-diazabicyclo<3.3.0>octane

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