(2Z,4S,5R,6E,8S,9R,10S,12S,13R)-1-tert-butyldiphenylsilyloxy-13-<3'-(2'',5''-dimethyl-pyrrol-1''-yl)-2',5'-dimethoxyphenyl>-5-triisopropylsilyloxy-10-methoxy-4,6,8,12-tetramethyl-2,6-tridecadien-9,13-diol

Base Information

• Chemical Name: (2Z,4S,5R,6E,8S,9R,10S,12S,13R)-1-tert-butyldiphenylsilyloxy-13-<3'-(2'',5''-dimethyl-pyrrol-1''-yl)-2',5'-dimethoxyphenyl>-5-triisopropylsilyloxy-10-methoxy-4,6,8,12-tetramethyl-2,6-tridecadien-9,13-diol
• CAS No.: 175356-54-4
• Molecular Formula: C₅₇H₈₇NO₇Si₂
• Molecular Weight: 954.491

Synonyms:(2Z,4S,5R,6E,8S,9R,10S,12S,13R)-1-tert-butyldiphenylsilyloxy-13-<3'-(2'',5''-dimethyl-pyrrol-1''-yl)-2',5'-dimethoxyphenyl>-5-triisopropylsilyloxy-10-methoxy-4,6,8,12-tetramethyl-2,6-tridecadien-9,13-diol

Chemical Property of (2Z,4S,5R,6E,8S,9R,10S,12S,13R)-1-tert-butyldiphenylsilyloxy-13-<3'-(2'',5''-dimethyl-pyrrol-1''-yl)-2',5'-dimethoxyphenyl>-5-triisopropylsilyloxy-10-methoxy-4,6,8,12-tetramethyl-2,6-tridecadien-9,13-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (2Z,4S,5R,6E,8S,9R,10S,12S,13R)-1-tert-butyldiphenylsilyloxy-13-<3'-(2'',5''-dimethyl-pyrrol-1''-yl)-2',5'-dimethoxyphenyl>-5-triisopropylsilyloxy-10-methoxy-4,6,8,12-tetramethyl-2,6-tridecadien-9,13-diol

There total 21 articles about (2Z,4S,5R,6E,8S,9R,10S,12S,13R)-1-tert-butyldiphenylsilyloxy-13-<3'-(2'',5''-dimethyl-pyrrol-1''-yl)-2',5'-dimethoxyphenyl>-5-triisopropylsilyloxy-10-methoxy-4,6,8,12-tetramethyl-2,6-tridecadien-9,13-diol 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:

furfural (98-01-1) → (2Z,4S,5R,6E,8S,9R,10S,12S,13R)-1-tert-butyldiphenylsilyloxy-13-<3'-(2'',5''-dimethyl-pyrrol-1''-yl)-2',5'-dimethoxyphenyl>-5-triisopropylsilyloxy-10-methoxy-4,6,8,12-tetramethyl-2,6-tridecadien-9,13-diol (175356-54-4)

Guidance literature:

Multi-step reaction with 21 steps

1: 1) n-Bu₂BOTf, Et₃N / CH₂Cl₂, -78 to 0 deg C

2: Br₂, H₂O / acetonitrile / -20 °C

3: 2,6-lutidine / CH₂Cl₂ / -78 °C

4: 97 percent / chlorotrimethylsilane / tetrahydrofuran / -78 °C

5: 1) NaBH₄, 2) DIBAL-H / 1) -20 deg C, 2) 0 deg C

6: 73 percent / NEt₃, DMAP / CH₂Cl₂ / Ambient temperature

7: Ph₃P, DEAD / benzene / Ambient temperature

8: NaOH / methanol / Ambient temperature

9: KH / tetrahydrofuran / 0 °C

10: CF₃CO₂H, H₂O / tetrahydrofuran / 0 °C

11: Pyr-SO₃, NEt₃ / dimethylsulfoxide / Ambient temperature

12: 1) sec-BuLi, 2) CF₃CO₂H, H₂O / 1) THF, -78 deg C, 2) 0 deg C

13: n-Bu₂BOTf, Et₃N / CH₂Cl₂, -78 to 0 deg C

14: AlMe₃ / CH₂Cl₂ / -40 - -10 °C

15: 2,6-lutidine / CH₂Cl₂ / 0 °C

16: DIBAL-H / tetrahydrofuran / -78 - -50 °C

17: KHMDS, 18-C-6 / tetrahydrofuran / -78 - -40 °C

18: DIBAL-H / tetrahydrofuran / -20 °C

19: DMAP / CH₂Cl₂ / Ambient temperature

20: 84 percent / aqueous HF / acetonitrile; tetrahydrofuran / Ambient temperature

21: TMEDA / diethyl ether / 0 deg C to room temperature

With 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium tetrahydroborate; chloro-trimethyl-silane; 18-crown-6 ether; N,N,N,N,-tetramethylethylenediamine; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; water; bromine; trimethylaluminum; sec.-butyllithium; sulfur trioxide pyridine complex; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; acetonitrile; benzene;

DOI:10.1021/jo00030a007

Reference yield:

<4R-<4α(2R*,3R*),5α>>-3-<3-(2-furanyl)-3-hydroxy-2-methyl-1-oxopropyl>-4-methyl-5-phenyl-2-oxazolidinone (95481-54-2) → (2Z,4S,5R,6E,8S,9R,10S,12S,13R)-1-tert-butyldiphenylsilyloxy-13-<3'-(2'',5''-dimethyl-pyrrol-1''-yl)-2',5'-dimethoxyphenyl>-5-triisopropylsilyloxy-10-methoxy-4,6,8,12-tetramethyl-2,6-tridecadien-9,13-diol (175356-54-4)

Guidance literature:

Multi-step reaction with 20 steps

1: Br₂, H₂O / acetonitrile / -20 °C

2: 2,6-lutidine / CH₂Cl₂ / -78 °C

3: 97 percent / chlorotrimethylsilane / tetrahydrofuran / -78 °C

4: 1) NaBH₄, 2) DIBAL-H / 1) -20 deg C, 2) 0 deg C

5: 73 percent / NEt₃, DMAP / CH₂Cl₂ / Ambient temperature

6: Ph₃P, DEAD / benzene / Ambient temperature

7: NaOH / methanol / Ambient temperature

8: KH / tetrahydrofuran / 0 °C

9: CF₃CO₂H, H₂O / tetrahydrofuran / 0 °C

10: Pyr-SO₃, NEt₃ / dimethylsulfoxide / Ambient temperature

11: 1) sec-BuLi, 2) CF₃CO₂H, H₂O / 1) THF, -78 deg C, 2) 0 deg C

12: n-Bu₂BOTf, Et₃N / CH₂Cl₂, -78 to 0 deg C

13: AlMe₃ / CH₂Cl₂ / -40 - -10 °C

14: 2,6-lutidine / CH₂Cl₂ / 0 °C

15: DIBAL-H / tetrahydrofuran / -78 - -50 °C

16: KHMDS, 18-C-6 / tetrahydrofuran / -78 - -40 °C

17: DIBAL-H / tetrahydrofuran / -20 °C

18: DMAP / CH₂Cl₂ / Ambient temperature

19: 84 percent / aqueous HF / acetonitrile; tetrahydrofuran / Ambient temperature

20: TMEDA / diethyl ether / 0 deg C to room temperature

With 2,6-dimethylpyridine; dmap; sodium hydroxide; sodium tetrahydroborate; chloro-trimethyl-silane; 18-crown-6 ether; N,N,N,N,-tetramethylethylenediamine; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; water; bromine; trimethylaluminum; sec.-butyllithium; sulfur trioxide pyridine complex; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; acetonitrile; benzene;

DOI:10.1021/jo00030a007

Reference yield:

O-tert-butyldimethylsilyl-2,6-dimethyl-7-O-(tert-butyldimethylsilyl)-2,3,6-trideoxy-β-L-gulo-heptopyranoside (136113-80-9) → (2Z,4S,5R,6E,8S,9R,10S,12S,13R)-1-tert-butyldiphenylsilyloxy-13-<3'-(2'',5''-dimethyl-pyrrol-1''-yl)-2',5'-dimethoxyphenyl>-5-triisopropylsilyloxy-10-methoxy-4,6,8,12-tetramethyl-2,6-tridecadien-9,13-diol (175356-54-4)

Guidance literature:

Multi-step reaction with 15 steps

1: Ph₃P, DEAD / benzene / Ambient temperature

2: NaOH / methanol / Ambient temperature

3: KH / tetrahydrofuran / 0 °C

4: CF₃CO₂H, H₂O / tetrahydrofuran / 0 °C

5: Pyr-SO₃, NEt₃ / dimethylsulfoxide / Ambient temperature

6: 1) sec-BuLi, 2) CF₃CO₂H, H₂O / 1) THF, -78 deg C, 2) 0 deg C

7: n-Bu₂BOTf, Et₃N / CH₂Cl₂, -78 to 0 deg C

8: AlMe₃ / CH₂Cl₂ / -40 - -10 °C

9: 2,6-lutidine / CH₂Cl₂ / 0 °C

10: DIBAL-H / tetrahydrofuran / -78 - -50 °C

11: KHMDS, 18-C-6 / tetrahydrofuran / -78 - -40 °C

12: DIBAL-H / tetrahydrofuran / -20 °C

13: DMAP / CH₂Cl₂ / Ambient temperature

14: 84 percent / aqueous HF / acetonitrile; tetrahydrofuran / Ambient temperature

15: TMEDA / diethyl ether / 0 deg C to room temperature

With 2,6-dimethylpyridine; dmap; sodium hydroxide; 18-crown-6 ether; N,N,N,N,-tetramethylethylenediamine; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; water; trimethylaluminum; sec.-butyllithium; sulfur trioxide pyridine complex; potassium hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; acetonitrile; benzene;

DOI:10.1021/jo00030a007

upstream raw materials:

furfural

<4R-<4α(2R^*,3R^*),5α>>-3-<3-(2-furanyl)-3-hydroxy-2-methyl-1-oxopropyl>-4-methyl-5-phenyl-2-oxazolidinone

O-tert-butyldimethylsilyl-2,6-dimethyl-7-O-(tert-butyldimethylsilyl)-2,3,6-trideoxy-β-L-gulo-heptopyranoside

O-tert-butyldimethylsilyl-2,6-dimethyl-7-O-(tert-butyldimethylsilyl)-4-O-(4-nitrobenzoate)-2,3,6-trideoxy-β-L-galacto-heptopyranoside

Downstream raw materials:

(2Z,4S,5R,6E,8S,9R,10S,12S,13R)-1-tert-butyldiphenylsilyloxy-13-<3'-(2'',5''-dimethyl-pyrrol-1''-yl)-2',5'-dimethoxyphenyl>-5-triisopropylsilyloxy-9,10,13-trimethoxy-4,6,8,12-tetramethyl-2,6-tridecadiene

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