(1S,2R,3R,7R,7aR)-3-Benzyloxymethyl-hexahydro-pyrrolizine-1,2,7-triol

Base Information

Chemical Name:(1S,2R,3R,7R,7aR)-3-Benzyloxymethyl-hexahydro-pyrrolizine-1,2,7-triol
CAS No.:618384-67-1
Molecular Formula:C₁₅H₂₁NO₄
Molecular Weight:279.336
Hs Code.:

Synonyms:

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Chemical Property of (1S,2R,3R,7R,7aR)-3-Benzyloxymethyl-hexahydro-pyrrolizine-1,2,7-triol

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Technology Process of (1S,2R,3R,7R,7aR)-3-Benzyloxymethyl-hexahydro-pyrrolizine-1,2,7-triol

There total 12 articles about (1S,2R,3R,7R,7aR)-3-Benzyloxymethyl-hexahydro-pyrrolizine-1,2,7-triol 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:

: 146916-76-9
5-(4-methoxyphenyl)methoxy-2-pentyn-1-ol

: 618384-67-1
(1S,2R,3R,7R,7aR)-3-Benzyloxymethyl-hexahydro-pyrrolizine-1,2,7-triol

Guidance literature:: Multi-step reaction with 11 steps

1: 89 percent / Red-Al / tetrahydrofuran; toluene / 4 h / 20 °C

2: T-BuOOH; CaH₂; D-(-)-diisopropyl tartrate / silica gel; Ti(O-i-Pr)4 / CH₂Cl₂ / 24 h / -20 °C

3: Et₃N; DMSO; (COCl)2 / CH₂Cl₂ / 0.42 h / -60 - 20 °C

4: 1.51 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 2 h / -10 °C

5: 98 percent / lithium triflate / acetonitrile / 72 h / 120 °C

6: 79 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

7: 82 percent / 4-morpholine N-oxide; K₂OsO₄*2H₂O / acetone; H₂O / 24 h / 20 °C

8: 76 percent / pyridine / 20 h / 20 °C

9: 88 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; H₂O / CH₂Cl₂ / 3 h / 20 °C

10: NaOH / ethanol / 24 h / 70 °C

11: PPh₃; pyridine; diisopropyl azodicarboxylate / 2.5 h / 0 °C

With pyridine; tert.-butylhydroperoxide; sodium hydroxide; potassium osmate(VI); calcium hydride; oxalyl dichloride; di-isopropyl azodicarboxylate; water; potassium hexamethylsilazane; lithium trifluoromethanesulfonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; titanium(IV) isopropylate; silica gel; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; toluene; acetonitrile; 3: Swern oxidation / 4: Wittig olefination;
DOI:10.1021/jo034914q

Reference yield:

: 158817-21-1
(E)-5-(4-methoxybenzyloxy)pent-2-en-1-ol

: 618384-67-1
(1S,2R,3R,7R,7aR)-3-Benzyloxymethyl-hexahydro-pyrrolizine-1,2,7-triol

Guidance literature:: Multi-step reaction with 10 steps

1: T-BuOOH; CaH₂; D-(-)-diisopropyl tartrate / silica gel; Ti(O-i-Pr)4 / CH₂Cl₂ / 24 h / -20 °C

2: Et₃N; DMSO; (COCl)2 / CH₂Cl₂ / 0.42 h / -60 - 20 °C

3: 1.51 g / potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 2 h / -10 °C

4: 98 percent / lithium triflate / acetonitrile / 72 h / 120 °C

5: 79 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

6: 82 percent / 4-morpholine N-oxide; K₂OsO₄*2H₂O / acetone; H₂O / 24 h / 20 °C

7: 76 percent / pyridine / 20 h / 20 °C

8: 88 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; H₂O / CH₂Cl₂ / 3 h / 20 °C

9: NaOH / ethanol / 24 h / 70 °C

10: PPh₃; pyridine; diisopropyl azodicarboxylate / 2.5 h / 0 °C

With pyridine; tert.-butylhydroperoxide; sodium hydroxide; potassium osmate(VI); calcium hydride; oxalyl dichloride; di-isopropyl azodicarboxylate; water; potassium hexamethylsilazane; lithium trifluoromethanesulfonate; D-(-)-diisopropyl tartrate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; titanium(IV) isopropylate; silica gel; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; toluene; acetonitrile; 2: Swern oxidation / 3: Wittig olefination;
DOI:10.1021/jo034914q