N-methoxy-N-methyl (2R,3S,5R)-5,7-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-3-[(triisopropyl-silyl)oxy]heptamide

Base Information

• Chemical Name: N-methoxy-N-methyl (2R,3S,5R)-5,7-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-3-[(triisopropyl-silyl)oxy]heptamide
• CAS No.: 366455-01-8
• Molecular Formula: C₃₁H₆₉NO₅Si₃
• Molecular Weight: 620.149

Synonyms:N-methoxy-N-methyl (2R,3S,5R)-5,7-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-3-[(triisopropyl-silyl)oxy]heptamide

Chemical Property of N-methoxy-N-methyl (2R,3S,5R)-5,7-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-3-[(triisopropyl-silyl)oxy]heptamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-methoxy-N-methyl (2R,3S,5R)-5,7-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-3-[(triisopropyl-silyl)oxy]heptamide

There total 1 articles about N-methoxy-N-methyl (2R,3S,5R)-5,7-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-3-[(triisopropyl-silyl)oxy]heptamide 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: 100.0%

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + (2R,3S,5R)-5,7-bis(tert-butyldimethylsilyl)oxy-3-hydroxy-N-methoxy-2-methyl-N-methylheptanamide (366455-00-7) → N-methoxy-N-methyl (2R,3S,5R)-5,7-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-3-[(triisopropyl-silyl)oxy]heptamide (366455-01-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 - 0 ℃; for 5h;

DOI:10.1021/ja011256n

Reference yield:

N-methoxy-N-methyl (2R,3S,5R)-5,7-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-3-[(triisopropyl-silyl)oxy]heptamide (366455-01-8) → (1S,4R,5R,7R,9R,13S,14S,15S)-3,11-dioxo-4-hydroxy-9-[(E)-2-iodoethenyl]-15-[[3-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.14,7]actadecane (215120-40-4)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 81 percent / DIBAL-H / tetrahydrofuran / 1.5 h / -78 °C

2.1: KHMDS; 18-crown-6 / tetrahydrofuran; toluene / 0.5 h / -78 °C

2.2: 94 percent / tetrahydrofuran; toluene / 1 h / -78 - 20 °C

3.1: PPTS / methanol; tetrahydrofuran / 17 h / 55 °C

4.1: 166 mg / K₂CO₃ / methanol; tetrahydrofuran / 3 h / Heating

5.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

6.1: 84 percent / K₂CO₃ / methanol / 2 h / 20 °C

7.1: 77 percent / 9-bromo-9-borobicyclo[3.3.1]nonane / CH₂Cl₂ / 3 h / 20 °C

8.1: CrCl₂; NiCl₂ / dimethylformamide / 72 h

9.1: PPTS / methanol / 35 °C

9.2: 87 percent / aq. NaOH / methanol / 20 °C

10.1: 2,4,6-Cl₃C₆H₂COCl; Et₃N / tetrahydrofuran / 20 °C

10.2: 46 percent / DMAP / tetrahydrofuran; toluene / Heating

11.1: 70 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

12.1: O₃ / CH₂Cl₂; methanol / -78 °C

12.2: 55 percent / Ph₃P / CH₂Cl₂; methanol / 20 °C

13.1: 71 percent / CrCl₂ / tetrahydrofuran / 20 °C

14.1: 97 percent / PPTS / methanol; CH₂Cl₂ / 20 °C

15.1: Dess-Martin periodinane / pyridine; CH₂Cl₂ / 0 °C

16.1: 1.5 mg / HF*pyridine / tetrahydrofuran; CH₂Cl₂ / 16 h

17.1: NBS; 4 Angstroem molecular sieves / acetonitrile / 0.83 h / -35 - 20 °C

With 2,6-dimethylpyridine; B-Br-9-BBN; chromium dichloride; N-Bromosuccinimide; 18-crown-6 ether; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; ozone; triethylamine; nickel dichloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 2.2: Wittig reaction / 5.1: Dess-Martin oxidation / 13.1: Takai reaction / 15.1: Dess-Martin oxidation;

DOI:10.1021/ja011256n

Reference yield:

N-methoxy-N-methyl (2R,3S,5R)-5,7-bis[(tert-butyldimethylsilyl)oxy]-2-methyl-3-[(triisopropyl-silyl)oxy]heptamide (366455-01-8) → 15-[4-(5-benzyloxy-3,4-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,5-dimethoxy-tetrahydro-pyran-2-yloxy]-4-hydroxy-9-(2-iodo-vinyl)-5,8,8,14-tetramethyl-10,17,18-trioxa-tricyclo[11.3.1.14,7]octadecane-3,11-dione

Guidance literature:

Multi-step reaction with 16 steps

1.1: 94 percent / DIBAL-H / tetrahydrofuran / 1 h / -78 °C

2.1: 18-crown-6; potassium, hexamethyldisilazide / tetrahydrofuran; toluene / 15 h / -78 °C

2.2: 83 percent / tetrahydrofuran; toluene / 3 h / -78 °C

3.1: 83 percent / PPTS / ethanol / 24 h / 55 °C

4.1: 88 percent / t-BuOK / tetrahydrofuran / 2 h / -50 °C

5.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

6.1: 84 percent / K₂CO₃ / methanol / 2 h / 20 °C

7.1: 9-bromo-9-borabicyclo[3.3.1]nonane / CH₂Cl₂ / 3 h / 20 °C

8.1: CrCl₂; NiCl₂ / dimethylformamide / 72 h

9.1: 87 percent / PPTS / methanol / 19 h / 35 °C

10.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1.5 h

10.2: 46 percent / DMAP / tetrahydrofuran; toluene / 0.25 h / Heating

11.1: 70 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

12.1: O₃ / CH₂Cl₂; methanol / 0.75 h / -78 °C

12.2: 81 percent / Ph₃P / CH₂Cl₂; methanol / 4.5 h / -78 - 20 °C

13.1: 71 percent / CrCl₂ / tetrahydrofuran / 4.5 h / 20 °C

14.1: 97 percent / PPTS / methanol; CH₂Cl₂ / 5.5 h / 20 °C

15.1: Dess-Martin periodinane / dimethylsulfoxide / 1.5 h / 0 °C

15.2: 87 percent / HF*pyridine / tetrahydrofuran; pyridine / 16 h

16.1: 27 percent / 4 Angstroem molecular sieves; N-bromosuccinimide / acetonitrile / 0.83 h / -35 - 20 °C

With 2,6-dimethylpyridine; B-Br-9-BBN; chromium dichloride; N-Bromosuccinimide; 18-crown-6 ether; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; potassium tert-butylate; potassium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; ozone; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; nickel dichloride; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 8.1: Nozaki-Hiyama-Kishi reaction / 10.2: Yamaguchi lactonization / 13.1: Takai reaction;

DOI:10.1021/jo0503862

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

(2R,3S,5R)-5,7-bis(tert-butyldimethylsilyl)oxy-3-hydroxy-N-methoxy-2-methyl-N-methylheptanamide

Downstream raw materials:

(1S,4R,5R,7R,9R,13S,14S,15S)-3,11-dioxo-4-hydroxy-9-[(E)-2-iodoethenyl]-15-[[3-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]actadecane

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