(2R,3S,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxy-ethyl)-3-azide-pyrrolidine

Base Information

Chemical Name:(2R,3S,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxy-ethyl)-3-azide-pyrrolidine
CAS No.:174193-30-7
Molecular Formula:C₂₀H₂₄N₄O₆S₂
Molecular Weight:480.566
Hs Code.:

Synonyms:(2R,3S,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxy-ethyl)-3-azide-pyrrolidine

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Chemical Property of (2R,3S,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxy-ethyl)-3-azide-pyrrolidine

Chemical Property:

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Technology Process of (2R,3S,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxy-ethyl)-3-azide-pyrrolidine

There total 10 articles about (2R,3S,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxy-ethyl)-3-azide-pyrrolidine 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%

: 98-59-9
p-toluenesulfonyl chloride

: 174193-29-4
(2R,3S,2'R)-N-tosyl-2-(1',2'-dihydroxyethyl)-3-azide-pyrrolidine

: 174193-30-7
(2R,3S,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxy-ethyl)-3-azide-pyrrolidine

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃;
DOI:10.1016/0040-4039(95)02041-1

Reference yield:

: 922-65-6
divinylcarbinol

: 174193-30-7
(2R,3S,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxy-ethyl)-3-azide-pyrrolidine

Guidance literature:: Multi-step reaction with 11 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: 82 percent / NaN₃ / dimethylformamide / 24 h / 90 °C

10: 85 percent / OsO₄, K₃Fe(CN)6, K₂CO₃, (DHQD)2PHAL / 2-methyl-propan-2-ol; H₂O / 24 h / Ambient temperature

11: 91 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; potassium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; sodium azide; 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; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1016/S0040-4020(96)01049-6

Reference yield:

: 100017-22-9
(S)-1-[(R)-oxiran-2-yl]prop-2-enol

: 174193-30-7
(2R,3S,2'R)-N-tosyl-2-(1'-tosyloxy-2'-hydroxy-ethyl)-3-azide-pyrrolidine

Guidance literature:: Multi-step reaction with 10 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: 82 percent / NaN₃ / dimethylformamide / 24 h / 90 °C

9: 85 percent / OsO₄, K₃Fe(CN)6, K₂CO₃, (DHQD)2PHAL / 2-methyl-propan-2-ol; H₂O / 24 h / Ambient temperature

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

With pyridine; hydrogenchloride; potassium hydroxide; osmium(VIII) oxide; lithium aluminium tetrahydride; sodium azide; potassium carbonate; toluene-4-sulfonic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; potassium hexacyanoferrate(III); In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1016/S0040-4020(96)01049-6