<2S(S),3R,6S,8S>-N-<6-hydroxy-2-(methoxycarbonyl)-3-<<2-(trimethylsilyl)ethoxy>methoxy>phenyl>-2-<1-<<1-<<2-(trimethylsilyl)ethoxy>methoxy>-2-pyrrolidyl>carbonyl>ethyl>-1,7-dioxaspiro<5.5>undecane-8-acetamide

Base Information

• Chemical Name: <2S(S),3R,6S,8S>-N-<6-hydroxy-2-(methoxycarbonyl)-3-<<2-(trimethylsilyl)ethoxy>methoxy>phenyl>-2-<1-<<1-<<2-(trimethylsilyl)ethoxy>methoxy>-2-pyrrolidyl>carbonyl>ethyl>-1,7-dioxaspiro<5.5>undecane-8-acetamide
• CAS No.: 142592-60-7
• Molecular Formula: C₃₉H₆₂N₂O₁₀Si₂
• Molecular Weight: 775.1
• Mol file: 142592-60-7.mol

Synonyms:

Chemical Property of <2S(S),3R,6S,8S>-N-<6-hydroxy-2-(methoxycarbonyl)-3-<<2-(trimethylsilyl)ethoxy>methoxy>phenyl>-2-<1-<<1-<<2-(trimethylsilyl)ethoxy>methoxy>-2-pyrrolidyl>carbonyl>ethyl>-1,7-dioxaspiro<5.5>undecane-8-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <2S(S),3R,6S,8S>-N-<6-hydroxy-2-(methoxycarbonyl)-3-<<2-(trimethylsilyl)ethoxy>methoxy>phenyl>-2-<1-<<1-<<2-(trimethylsilyl)ethoxy>methoxy>-2-pyrrolidyl>carbonyl>ethyl>-1,7-dioxaspiro<5.5>undecane-8-acetamide

There total 29 articles about <2S(S),3R,6S,8S>-N-<6-hydroxy-2-(methoxycarbonyl)-3-<<2-(trimethylsilyl)ethoxy>methoxy>phenyl>-2-<1-<<1-<<2-(trimethylsilyl)ethoxy>methoxy>-2-pyrrolidyl>carbonyl>ethyl>-1,7-dioxaspiro<5.5>undecane-8-acetamide 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:

(S)-1-(benzyloxy)-3-hydroxyhex-5-ene (91285-62-0,111322-01-1,119239-98-4) → <2S(S),3R,6S,8S>-N-<6-hydroxy-2-(methoxycarbonyl)-3-<<2-(trimethylsilyl)ethoxy>methoxy>phenyl>-2-<1-<<1-<<2-(trimethylsilyl)ethoxy>methoxy>-2-pyrrolidyl>carbonyl>ethyl>-1,7-dioxaspiro<5.5>undecane-8-acetamide (142592-60-7)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) 9-borabicyclo<3.3.1>nonane, 2.) 3N aq. NaOH, 30percent H₂O₂ / 1.) THF, 65 deg C, 3 h, 2.) 1 h, r.t.

2: 97 percent / camphorsulphonic acid / CH₂Cl₂ / 1 h / Ambient temperature

3: 80 percent / H₂ / 10percent Pd/C / ethanol / 12 h / Ambient temperature

4: 88 percent / camphorsulphonic acid, CuSO₄ / acetone / 10 h / Ambient temperature

5: Et₃N / CH₂Cl₂ / 1 h

6: NaI / acetone / 3 h / 40 °C

8: 76 percent / NaH / paraffin; tetrahydrofuran / 3 h / Ambient temperature

9: 71 percent / n-Bu₄NF / tetrahydrofuran / 8 h / Ambient temperature

10: 1.) 4-methylmorpholine-N-oxide (NMO), 4 Angstroem molecular sieves, 2.) tetra-n-propylammonium perruthenate (TPAP) / 1.) CH₂Cl₂, 10 min, r.t., 2.) 1 h

11: 1.) BuLi / 1.) hexane, DME, a) -10 deg C, 20 min, b) 0 deg C, 0.5 h, 2.) THF, DME, a) -10 deg C, 0.5 h, b) -10 deg C to r.t., 2 h

12: 1.) 4-methylmorpholine-N-oxide (NMO), 4 Angstroem molecular sieves, 2.) tetra-n-propylammonium perruthenate (TPAP) / 1.) CH₃CN, 10 min, r.t., 2.) 3 h

13: 86 percent / H₂ / 10percent Pd/C / ethanol / 5 h / Ambient temperature

14: 84 percent / CrO₃, conc. H₂SO₄ / H₂O; acetone / 1 h / -25 - -5 °C

15: 1.) ClCO₂Et, Et₃N / 1.) CH₂Cl₂, -10 deg C, 30 min, 2.) THF, a) -10 deg C, 1 h, b) 16 h, r.t.

With chromium(VI) oxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; tetrapropylammonium perruthennate; 4 A molecular sieve; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; chloroformic acid ethyl ester; sodium hydride; copper(II) sulfate; 4-methylmorpholine N-oxide; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; paraffin;

DOI:10.1016/S0040-4020(01)80467-1

Reference yield:

(S)-methyl-7-(benzyloxy)-5-hydroxy-2-heptenoate (144604-65-9) → <2S(S),3R,6S,8S>-N-<6-hydroxy-2-(methoxycarbonyl)-3-<<2-(trimethylsilyl)ethoxy>methoxy>phenyl>-2-<1-<<1-<<2-(trimethylsilyl)ethoxy>methoxy>-2-pyrrolidyl>carbonyl>ethyl>-1,7-dioxaspiro<5.5>undecane-8-acetamide (142592-60-7)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂ / PtO₂/C / CH₂Cl₂ / 4 h / Ambient temperature

3: 1.) 4-methylmorpholine-N-oxide (NMO), 4 Angstroem molecular sieves, 2.) tetra-n-propylammonium perruthenate (TPAP) / 1.) CH₂Cl₂, 10 min, r.t., 2.) 1 h

4: 1.) BuLi / 1.) hexane, DME, a) -10 deg C, 20 min, b) 0 deg C, 0.5 h, 2.) THF, DME, a) -10 deg C, 0.5 h, b) -10 deg C to r.t., 2 h

5: 1.) 4-methylmorpholine-N-oxide (NMO), 4 Angstroem molecular sieves, 2.) tetra-n-propylammonium perruthenate (TPAP) / 1.) CH₃CN, 10 min, r.t., 2.) 3 h

6: 86 percent / H₂ / 10percent Pd/C / ethanol / 5 h / Ambient temperature

7: 84 percent / CrO₃, conc. H₂SO₄ / H₂O; acetone / 1 h / -25 - -5 °C

8: 1.) ClCO₂Et, Et₃N / 1.) CH₂Cl₂, -10 deg C, 30 min, 2.) THF, a) -10 deg C, 1 h, b) 16 h, r.t.

With chromium(VI) oxide; n-butyllithium; tetrapropylammonium perruthennate; 4 A molecular sieve; sulfuric acid; hydrogen; chloroformic acid ethyl ester; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; PtO₂/C; In ethanol; dichloromethane; water; acetone;

DOI:10.1016/S0040-4020(01)80467-1

Reference yield:

(S)-7-Benzyloxy-5-hydroxy-heptanoic acid methyl ester → <2S(S),3R,6S,8S>-N-<6-hydroxy-2-(methoxycarbonyl)-3-<<2-(trimethylsilyl)ethoxy>methoxy>phenyl>-2-<1-<<1-<<2-(trimethylsilyl)ethoxy>methoxy>-2-pyrrolidyl>carbonyl>ethyl>-1,7-dioxaspiro<5.5>undecane-8-acetamide (142592-60-7)

Guidance literature:

Multi-step reaction with 7 steps

2: 1.) 4-methylmorpholine-N-oxide (NMO), 4 Angstroem molecular sieves, 2.) tetra-n-propylammonium perruthenate (TPAP) / 1.) CH₂Cl₂, 10 min, r.t., 2.) 1 h

3: 1.) BuLi / 1.) hexane, DME, a) -10 deg C, 20 min, b) 0 deg C, 0.5 h, 2.) THF, DME, a) -10 deg C, 0.5 h, b) -10 deg C to r.t., 2 h

4: 1.) 4-methylmorpholine-N-oxide (NMO), 4 Angstroem molecular sieves, 2.) tetra-n-propylammonium perruthenate (TPAP) / 1.) CH₃CN, 10 min, r.t., 2.) 3 h

5: 86 percent / H₂ / 10percent Pd/C / ethanol / 5 h / Ambient temperature

6: 84 percent / CrO₃, conc. H₂SO₄ / H₂O; acetone / 1 h / -25 - -5 °C

7: 1.) ClCO₂Et, Et₃N / 1.) CH₂Cl₂, -10 deg C, 30 min, 2.) THF, a) -10 deg C, 1 h, b) 16 h, r.t.

With chromium(VI) oxide; n-butyllithium; tetrapropylammonium perruthennate; 4 A molecular sieve; sulfuric acid; hydrogen; chloroformic acid ethyl ester; 4-methylmorpholine N-oxide; triethylamine; palladium on activated charcoal; In ethanol; water; acetone;

DOI:10.1016/S0040-4020(01)80467-1

upstream raw materials:

methyl 2-amino-3-hydroxy-6-<<2-(trimethylsilyl)ethoxy>methoxy> benzoate

<2S(S),3R,6S,8S>-3-methyl-2-<1-<<1-<<2-(trimethylsilyl)ethoxy>methoxy>-2-pyrrolidyl>carbonyl>ethyl>-1,7-dioxaspiro<5.5>undecane-8-acetic acid

Methyl 2,5-dihydroxybenzoate

methyl 2-hydroxy-5-(phenylmethoxy)benzoate

Downstream raw materials:

Routiennocin