2-{(3S,4R,5S,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide

Base Information

• Chemical Name: 2-{(3S,4R,5S,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide
• CAS No.: 115118-80-4
• Molecular Formula: C₂₇H₃₉NO₅Si
• Molecular Weight: 485.696
• Mol file: 115118-80-4.mol

Synonyms:2-{(3S,4R,5S,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide

Chemical Property of 2-{(3S,4R,5S,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{(3S,4R,5S,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide

There total 10 articles about 2-{(3S,4R,5S,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-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: 90.0%

(2S-cis)-5,6-dihydro-N,N-dimethyl-2-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-acetamide (115140-92-6) → 2-{(3S,4R,5R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide (115118-80-4)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; for 24h; Ambient temperature;

DOI:10.1021/jo00253a021

Reference yield: 90.0%

2-{(3S,4R,5R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-5-hydroxy-4-methoxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide → 2-{(3S,4R,5S,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide (115118-80-4)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone;

DOI:10.1021/jo00383a046

Reference yield:

(2S,3S)-2-(2-Hydroxy-ethyl)-3,6-dihydro-2H-pyran-3-ol → 2-{(3S,4R,5R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4,5-dihydroxy-tetrahydro-pyran-3-yl}-N,N-dimethyl-acetamide (115118-80-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 2 h / 0 - 20 °C

2: 100 percent / xylene / 12 h / Heating

3: 90 percent / N-methylmorpholine N-oxide, OsO₄ / acetone; H₂O / 24 h / Ambient temperature

With pyridine; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; xylene;

DOI:10.1021/jo00253a021

upstream raw materials:

(2S-cis)-5,6-dihydro-N,N-dimethyl-2-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2H-pyran-5-acetamide

3,5-hexadienoyl chloride

(3aS)-3,3a,5,7a-tetrahydro-2H-furo<3,2-b>pyran-2-one

(3aS,7R,7aR)-7-Iodo-hexahydro-furo[3,2-b]pyran-2-one

Downstream raw materials:

<3aS-<3aα,4α,7aα,7α(3E,2S^*)>>-tetrahydro-2,2-dimethyl-4-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-α(1-propenyl)-4H-1,3-dioxolo<4,5-c>pyran-7-ethanol<<(1,1-dimethylethyl)dimethylsilyl>oxy>acetate

<3aS)-(3aα,4α,7aα,7α)>-1-oxy>ethyl>-1,3-dioxolo<4,5-c>pyran-7-yl>-3-pentyn-2-one

(R)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-yn-2-ol

(E)-(R)-1-{(3aS,4S,7S,7aR)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl}-pent-3-en-2-ol