(Z)-7-[(2S,3R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-4-oxo-tetrahydro-pyran-3-yl]-hept-5-enoic acid methyl ester

Base Information

• Chemical Name: (Z)-7-[(2S,3R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-4-oxo-tetrahydro-pyran-3-yl]-hept-5-enoic acid methyl ester
• CAS No.: 78081-19-3
• Molecular Formula: C₃₁H₄₂O₆Si
• Molecular Weight: 538.756
• Mol file: 78081-19-3.mol

Synonyms:(Z)-7-[(2S,3R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-4-oxo-tetrahydro-pyran-3-yl]-hept-5-enoic acid methyl ester

Chemical Property of (Z)-7-[(2S,3R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-4-oxo-tetrahydro-pyran-3-yl]-hept-5-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-7-[(2S,3R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-4-oxo-tetrahydro-pyran-3-yl]-hept-5-enoic acid methyl ester

There total 1 articles about (Z)-7-[(2S,3R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-4-oxo-tetrahydro-pyran-3-yl]-hept-5-enoic acid methyl ester 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: 86.0%

(Z)-7-[(2S,3S,4S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl]-hept-5-enoic acid methyl ester (65011-74-7) → (Z)-7-[(2S,3R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-4-oxo-tetrahydro-pyran-3-yl]-hept-5-enoic acid methyl ester (78081-19-3)

Guidance literature:

With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic anhydride; In dimethyl sulfoxide; for 3h;

DOI:10.1139/v81-126

Reference yield: 74.0%

(Z)-7-[(2S,3R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-4-oxo-tetrahydro-pyran-3-yl]-hept-5-enoic acid methyl ester (78081-19-3) → (Z)-7-[(2S,3S,4S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl]-hept-5-enoic acid methyl ester (65011-74-7)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃;

DOI:10.1139/v81-126

Reference yield:

(Z)-7-[(2S,3R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-4-oxo-tetrahydro-pyran-3-yl]-hept-5-enoic acid methyl ester (78081-19-3) → Benzoic acid (2R,3S,4S,6S)-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-2-((E)-3-oxo-oct-1-enyl)-tetrahydro-pyran-4-yl ester (65011-78-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 74 percent / sodium borohydride / methanol / 0 °C

2: 89 percent / pyridine / Ambient temperature

3: 89.5 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

4: 91 percent / chromium trioxide-pyridine, / CH₂Cl₂ / 30 h

5: 79 percent / diethyl ether / 3 h / Ambient temperature

With pyridine; sodium tetrahydroborate; chromium trioxide pyridine; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1139/v81-126

upstream raw materials:

(Z)-7-[(2S,3S,4S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl]-hept-5-enoic acid methyl ester

Downstream raw materials:

(Z)-7-[(2S,3S,4S,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-6-methoxy-tetrahydro-pyran-3-yl]-hept-5-enoic acid methyl ester

Benzoic acid (2S,3S,4S,6S)-2-formyl-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester

Benzoic acid (2S,3S,4S,6S)-2-hydroxymethyl-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-tetrahydro-pyran-4-yl ester

Benzoic acid (2R,3S,4S,6S)-6-methoxy-3-((Z)-6-methoxycarbonyl-hex-2-enyl)-2-((E)-3-oxo-oct-1-enyl)-tetrahydro-pyran-4-yl ester