(3S)-3-benzyloxy-3-<(2S,3R)-1-<(benzyloxy)carbonyl>-3-hydroxy-2-pyrrolidinyl>-1-propanol

Base Information

• Chemical Name: (3S)-3-benzyloxy-3-<(2S,3R)-1-<(benzyloxy)carbonyl>-3-hydroxy-2-pyrrolidinyl>-1-propanol
• CAS No.: 143377-02-0
• Molecular Formula: C₂₂H₂₇NO₅
• Molecular Weight: 385.46

Synonyms:

Chemical Property of (3S)-3-benzyloxy-3-<(2S,3R)-1-<(benzyloxy)carbonyl>-3-hydroxy-2-pyrrolidinyl>-1-propanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-3-benzyloxy-3-<(2S,3R)-1-<(benzyloxy)carbonyl>-3-hydroxy-2-pyrrolidinyl>-1-propanol

There total 16 articles about (3S)-3-benzyloxy-3-<(2S,3R)-1-<(benzyloxy)carbonyl>-3-hydroxy-2-pyrrolidinyl>-1-propanol 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:

(1,2:5,6)-di-O-isopropylidene-D-gulose (14686-89-6) → (3S)-3-benzyloxy-3-<(2S,3R)-1-<(benzyloxy)carbonyl>-3-hydroxy-2-pyrrolidinyl>-1-propanol (143377-02-0)

Guidance literature:

Multi-step reaction with 14 steps

1: 95 percent / pyridine

2: 74 percent / 0.8percent aq. H₂SO₄ / dioxane; methanol / 23 h / Ambient temperature

3: 94 percent / CBr₄, PPh₃ / tetrahydrofuran / 11 h / Ambient temperature

4: 96 percent / NaN₃ / dimethylformamide / 8 h / 45 °C

5: H₂ / Raney nickel / methanol / 24 h / Ambient temperature

6: NaOAc / ethanol / 15 h / Heating

7: Na₂CO₃ / acetone; H₂O / 2 h / 0 °C

8: 99 percent / 2,4,5-triiodoimidazole, PPh₃ / toluene / 4 h / Heating

9: 97 percent / Bu₃SnH, AIBN / benzene / 3 h / Heating

10: 94 percent / HCl / diethyl ether / 15 h / Ambient temperature

11: 1) KH / 1) DMF, RT, 30 min

12: 86 percent / 50percent aq. TFA / 5 h / 50 °C

13: 1) n-BuLi / 1) THF, hexane, RT, 2) THF, 45 deg C, 5 h

14: 1) disiamylborane, 2) 2N NaOH, 30percent H₂O₂ / 1) THF, 3 h, 2) RT, 8 h

With pyridine; hydrogenchloride; sodium hydroxide; 2,4,5-triiodoimidazole; n-butyllithium; sodium azide; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; sulfuric acid; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium acetate; bis-(1,2-dimethylpropyl)borane; potassium hydride; sodium carbonate; triphenylphosphine; trifluoroacetic acid; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1016/S0040-4020(01)80323-9

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → (3S)-3-benzyloxy-3-<(2S,3R)-1-<(benzyloxy)carbonyl>-3-hydroxy-2-pyrrolidinyl>-1-propanol (143377-02-0)

Guidance literature:

Multi-step reaction with 15 steps

1: NaBH₄ / ethanol

2: 95 percent / pyridine

3: 74 percent / 0.8percent aq. H₂SO₄ / dioxane; methanol / 23 h / Ambient temperature

4: 94 percent / CBr₄, PPh₃ / tetrahydrofuran / 11 h / Ambient temperature

5: 96 percent / NaN₃ / dimethylformamide / 8 h / 45 °C

6: H₂ / Raney nickel / methanol / 24 h / Ambient temperature

7: NaOAc / ethanol / 15 h / Heating

8: Na₂CO₃ / acetone; H₂O / 2 h / 0 °C

9: 99 percent / 2,4,5-triiodoimidazole, PPh₃ / toluene / 4 h / Heating

10: 97 percent / Bu₃SnH, AIBN / benzene / 3 h / Heating

11: 94 percent / HCl / diethyl ether / 15 h / Ambient temperature

12: 1) KH / 1) DMF, RT, 30 min

13: 86 percent / 50percent aq. TFA / 5 h / 50 °C

14: 1) n-BuLi / 1) THF, hexane, RT, 2) THF, 45 deg C, 5 h

15: 1) disiamylborane, 2) 2N NaOH, 30percent H₂O₂ / 1) THF, 3 h, 2) RT, 8 h

With pyridine; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; 2,4,5-triiodoimidazole; n-butyllithium; sodium azide; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; sulfuric acid; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium acetate; bis-(1,2-dimethylpropyl)borane; potassium hydride; sodium carbonate; triphenylphosphine; trifluoroacetic acid; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1016/S0040-4020(01)80323-9

Reference yield:

1,2:5,6-di-O-isopropylidene-3-O-(methylsulphonyl)-α-D-allofuranose (14728-80-4) → (3S)-3-benzyloxy-3-<(2S,3R)-1-<(benzyloxy)carbonyl>-3-hydroxy-2-pyrrolidinyl>-1-propanol (143377-02-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 74 percent / 0.8percent aq. H₂SO₄ / dioxane; methanol / 23 h / Ambient temperature

2: 94 percent / CBr₄, PPh₃ / tetrahydrofuran / 11 h / Ambient temperature

3: 96 percent / NaN₃ / dimethylformamide / 8 h / 45 °C

4: H₂ / Raney nickel / methanol / 24 h / Ambient temperature

5: NaOAc / ethanol / 15 h / Heating

6: Na₂CO₃ / acetone; H₂O / 2 h / 0 °C

7: 99 percent / 2,4,5-triiodoimidazole, PPh₃ / toluene / 4 h / Heating

8: 97 percent / Bu₃SnH, AIBN / benzene / 3 h / Heating

9: 94 percent / HCl / diethyl ether / 15 h / Ambient temperature

10: 1) KH / 1) DMF, RT, 30 min

11: 86 percent / 50percent aq. TFA / 5 h / 50 °C

12: 1) n-BuLi / 1) THF, hexane, RT, 2) THF, 45 deg C, 5 h

13: 1) disiamylborane, 2) 2N NaOH, 30percent H₂O₂ / 1) THF, 3 h, 2) RT, 8 h

With hydrogenchloride; sodium hydroxide; 2,4,5-triiodoimidazole; n-butyllithium; sodium azide; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; sulfuric acid; hydrogen; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium acetate; bis-(1,2-dimethylpropyl)borane; potassium hydride; sodium carbonate; triphenylphosphine; trifluoroacetic acid; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1016/S0040-4020(01)80323-9

upstream raw materials:

(-)-(2S,3R)-1-<(benzyloxy)carbonyl>-2-<(S)-1-(benzyloxy)prop-2-enyl>-3-hydroxypyrrolidine

(1,2:5,6)-di-O-isopropylidene-D-gulose

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose

1,2:5,6-di-O-isopropylidene-3-O-(methylsulphonyl)-α-D-allofuranose

Downstream raw materials:

(S)-1-<(2R,3R)-3-acetoxy-1-<(benzyloxy)carbonyl>-2-pyrrolidinyl>-1-benzyloxy-3-<(tert-butyldimethylsilyl)oxy>-propane

detoxin D&%1

(S)-1-<(2R,3R)-3-acetoxy-1--2-pyrrolidinyl>-1-benzyloxy-3-<(tert-butyldimethylsilyl)oxy>-propane

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