tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-erythro-dodeca-8E-enopyranoside

Base Information

• Chemical Name: tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-erythro-dodeca-8E-enopyranoside
• CAS No.: 167901-90-8
• Molecular Formula: C₂₃H₃₆O₃
• Molecular Weight: 360.537
• Mol file: 167901-90-8.mol

Synonyms:

Chemical Property of tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-erythro-dodeca-8E-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-erythro-dodeca-8E-enopyranoside

There total 4 articles about tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-erythro-dodeca-8E-enopyranoside 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:

(2R,3S,6R)-3-Benzyloxy-6-tert-butoxy-2-[2-(3-propyl-oxiranyl)-ethyl]-tetrahydro-pyran → tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-erythro-dodeca-8E-enopyranoside (167901-90-8)

Guidance literature:

(2R,3S,6R)-3-Benzyloxy-6-tert-butoxy-2-[2-(3-propyl-oxiranyl)-ethyl]-tetrahydro-pyran; With lithium diphenylphosphide; In tetrahydrofuran; hexane; at 20 ℃; for 2h;

With methyl iodide; In tetrahydrofuran; hexane; for 1h;

DOI:10.1081/CAR-120014903

Reference yield:

tert-butyl 4-O-benzyl-2,3,6,7,8,9-hexadeoxy-α-D-erythro-non-8-enopyranoside (167901-80-6) → tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-erythro-dodeca-8E-enopyranoside (167901-90-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: O₃ / CH₂Cl₂; methanol / -78 °C

1.2: PPh₃ / CH₂Cl₂; methanol / 1 h / 20 °C

2.1: sodium bis(trimethylsilyl)amide / hexane; toluene / 1 h / 20 °C

2.2: hexane; toluene / -78 - 20 °C

3.1: 50 percent MCPBA; 4 M NaH₂PO₄; Na₂HPO₄ / CH₂Cl₂ / 1 h / 20 °C

4.1: Ph₂PLi / tetrahydrofuran; hexane / 2 h / 20 °C

4.2: MeI / tetrahydrofuran; hexane / 1 h

With disodium hydrogenphosphate; sodium dihydrogenphosphate; sodium hexamethyldisilazane; ozone; 3-chloro-benzenecarboperoxoic acid; lithium diphenylphosphide; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 2.1: Wittig reaction;

DOI:10.1081/CAR-120014903

Reference yield:

tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-erythro-dodeca-8Z-enopyranoside (167901-86-2) → tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-erythro-dodeca-8E-enopyranoside (167901-90-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 50 percent MCPBA; 4 M NaH₂PO₄; Na₂HPO₄ / CH₂Cl₂ / 1 h / 20 °C

2.1: Ph₂PLi / tetrahydrofuran; hexane / 2 h / 20 °C

2.2: MeI / tetrahydrofuran; hexane / 1 h

With disodium hydrogenphosphate; sodium dihydrogenphosphate; 3-chloro-benzenecarboperoxoic acid; lithium diphenylphosphide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1081/CAR-120014903

upstream raw materials:

tert-butyl 4-O-benzyl-2,3,6,7,8,9-hexadeoxy-α-D-erythro-non-8-enopyranoside

tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-erythro-dodeca-8Z-enopyranoside

Downstream raw materials:

(S)-4-Benzyloxy-4-[(2R,5S)-5-((S)-1-iodo-butyl)-tetrahydro-furan-2-yl]-butyraldehyde

(S)-4-Benzyloxy-4-[(2R,5R)-5-((R)-1-iodo-butyl)-tetrahydro-furan-2-yl]-butyraldehyde