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

Base Information

• Chemical Name: (S)-1-<(2R,3R)-3-acetoxy-1--2-pyrrolidinyl>-1-benzyloxy-3-<(tert-butyldimethylsilyl)oxy>-propane
• CAS No.: 143367-60-6
• Molecular Formula: C₃₂H₅₄N₂O₇Si
• Molecular Weight: 606.875

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

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

Chemical Property:

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

There total 20 articles about (S)-1-<(2R,3R)-3-acetoxy-1--2-pyrrolidinyl>-1-benzyloxy-3-<(tert-butyldimethylsilyl)oxy>-propane 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: 90.0%

t-Boc-L-valine (13734-41-3) + Acetic acid (2R,3R)-2-[(S)-1-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-pyrrolidin-3-yl ester → (S)-1-<(2R,3R)-3-acetoxy-1--2-pyrrolidinyl>-1-benzyloxy-3-<(tert-butyldimethylsilyl)oxy>-propane (143367-60-6)

Guidance literature:

With bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; In dichloromethane; at -15 ℃; for 0.333333h;

DOI:10.1016/S0040-4039(00)92511-5

Reference yield:

(1,2:5,6)-di-O-isopropylidene-D-gulose (14686-89-6) → (S)-1-<(2R,3R)-3-acetoxy-1--2-pyrrolidinyl>-1-benzyloxy-3-<(tert-butyldimethylsilyl)oxy>-propane (143367-60-6)

Guidance literature:

Multi-step reaction with 18 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

15: NEt₃, 4-dimethylaminopyridine / CH₂Cl₂ / 18 h / Ambient temperature

16: NEt₃ / CH₂Cl₂ / 2 h

17: H₂ / Raney nickel / methanol; ethyl acetate / 2 h / 2068.6 Torr

18: N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride, NEt₃ / CH₂Cl₂ / 0.5 h / -15 °C

With pyridine; hydrogenchloride; dmap; 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-(2-oxo-3-oxazolidinyl)phosphoryl chloride; bis-(1,2-dimethylpropyl)borane; potassium hydride; sodium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; 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) → (S)-1-<(2R,3R)-3-acetoxy-1--2-pyrrolidinyl>-1-benzyloxy-3-<(tert-butyldimethylsilyl)oxy>-propane (143367-60-6)

Guidance literature:

Multi-step reaction with 19 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

16: NEt₃, 4-dimethylaminopyridine / CH₂Cl₂ / 18 h / Ambient temperature

17: NEt₃ / CH₂Cl₂ / 2 h

18: H₂ / Raney nickel / methanol; ethyl acetate / 2 h / 2068.6 Torr

19: N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride, NEt₃ / CH₂Cl₂ / 0.5 h / -15 °C

With pyridine; hydrogenchloride; dmap; 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-(2-oxo-3-oxazolidinyl)phosphoryl chloride; bis-(1,2-dimethylpropyl)borane; potassium hydride; sodium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; nickel; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; benzene;

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

upstream raw materials:

t-Boc-L-valine

(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:

detoxin D&%1

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