(5S,6R)-5-Benzyloxy-6,7-dihydroxy-heptanenitrile

Base Information

• Chemical Name: (5S,6R)-5-Benzyloxy-6,7-dihydroxy-heptanenitrile
• CAS No.: 132047-76-8
• Molecular Formula: C₁₄H₁₉NO₃
• Molecular Weight: 249.31
• Mol file: 132047-76-8.mol

Synonyms:(5S,6R)-5-Benzyloxy-6,7-dihydroxy-heptanenitrile

Chemical Property of (5S,6R)-5-Benzyloxy-6,7-dihydroxy-heptanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6R)-5-Benzyloxy-6,7-dihydroxy-heptanenitrile

There total 6 articles about (5S,6R)-5-Benzyloxy-6,7-dihydroxy-heptanenitrile 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: 84.0%

(5S,6R)-5-(benzyloxy)-6,7-dihydroxyheptanenitrile 6,7-acetonitrile (100818-76-6) → (5S,6R)-5-Benzyloxy-6,7-dihydroxy-heptanenitrile (132047-76-8)

Guidance literature:

With acetic acid; In methanol; for 8h; Heating;

DOI:10.1021/jo00003a049

Reference yield:

(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol (79364-35-5) → (5S,6R)-5-Benzyloxy-6,7-dihydroxy-heptanenitrile (132047-76-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) NaH / 1) DMF, 0 deg C, 15 min, 2) 23 deg C, 2h

2: 1) 1M BH₃*THF, 2) 3M NaOH, 30percent H₂O₂ / 1) 23 deg C, 2h, 2) 23 deg C, 2.3h

3: NEt₃ / CH₂Cl₂ / 0.33 h / 0 °C

4: n-Bu₄NI / dimethylformamide / 2 h / 80 °C

5: 84 percent / 50percent HOAc / methanol / 8 h / Heating

With sodium hydroxide; borane-THF; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00003a049

Reference yield:

benzyl bromide (100-39-0) → (5S,6R)-5-Benzyloxy-6,7-dihydroxy-heptanenitrile (132047-76-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) NaH / 1) DMF, 0 deg C, 15 min, 2) 23 deg C, 2h

2: 1) 1M BH₃*THF, 2) 3M NaOH, 30percent H₂O₂ / 1) 23 deg C, 2h, 2) 23 deg C, 2.3h

3: NEt₃ / CH₂Cl₂ / 0.33 h / 0 °C

4: n-Bu₄NI / dimethylformamide / 2 h / 80 °C

5: 84 percent / 50percent HOAc / methanol / 8 h / Heating

With sodium hydroxide; borane-THF; dihydrogen peroxide; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00003a049

upstream raw materials:

(5S,6R)-5-(benzyloxy)-6,7-dihydroxyheptanenitrile 6,7-acetonitrile

(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

benzyl bromide

(R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane

Downstream raw materials:

methyl 1α-(benzyloxy)-8-bromo-6β-(3'-hydroxy-prop-2'-en-1'-yl)-5β-methyl-1,2,3,4aα,5,6,8aα-octahydronaphthalene-5α-carboxylate

methyl 1α-(benzyloxy)-8-bromo-6β-(3'-hydroxyprop-2'-en-1'-yl)-5α-methyl-1,2,3,4aβ,5,6,8aα-octahydronaphthalene-5β-carboxylate

methyl (2E,7S,8Z,10E)-7-(benzyloxy)-9-bromo-12-hydroxy-2-methyldodeca-2,8,10-trienoate

(2E,4E,6Z)-(S)-8-Benzyloxy-6-bromo-11-cyano-undeca-2,4,6-trienoic acid ethyl ester