(6S)-6-O-benzyl-1,2:3,4-di-O-isopropylidene-6-(2-thiazolyl)-α-D-galacto-hexo-1,5-pyranose

Base Information

• Chemical Name: (6S)-6-O-benzyl-1,2:3,4-di-O-isopropylidene-6-(2-thiazolyl)-α-D-galacto-hexo-1,5-pyranose
• CAS No.: 118377-18-7
• Molecular Formula: C₂₂H₂₇NO₆S
• Molecular Weight: 433.525
• Mol file: 118377-18-7.mol

Synonyms:

Chemical Property of (6S)-6-O-benzyl-1,2:3,4-di-O-isopropylidene-6-(2-thiazolyl)-α-D-galacto-hexo-1,5-pyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S)-6-O-benzyl-1,2:3,4-di-O-isopropylidene-6-(2-thiazolyl)-α-D-galacto-hexo-1,5-pyranose

There total 3 articles about (6S)-6-O-benzyl-1,2:3,4-di-O-isopropylidene-6-(2-thiazolyl)-α-D-galacto-hexo-1,5-pyranose 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:

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde (4933-77-1) → (6S)-6-O-benzyl-1,2:3,4-di-O-isopropylidene-6-(2-thiazolyl)-α-D-galacto-hexo-1,5-pyranose (118377-18-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) n-tetrabutylammonium fluoride / 1.) CH₂Cl₂, room temp., overnight 2.) THF, 1-2 h

2: NaH, n-tetrabutylammonium iodide / tetrahydrofuran / Ambient temperature

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)81646-X

Reference yield:

2-[((3aR,5S,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-trimethylsilanyloxy-methyl]-thiazole → (6S)-6-O-benzyl-1,2:3,4-di-O-isopropylidene-6-(2-thiazolyl)-α-D-galacto-hexo-1,5-pyranose (118377-18-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1 M tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h

2: 1.) NaH, 2.) tetra-n-butylammonium iodide / 1.) THF, reflux, 20 min, 2.) room temp., overnight

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;

DOI:10.1021/jo00264a035

Reference yield:

benzyl bromide (100-39-0) + (6S)-1,2:3,4-di-O-isopropylidene-6-(2-thiazolyl)-α-D-galacto-hexo-1,5-pyranose (115244-00-3) → (6S)-6-O-benzyl-1,2:3,4-di-O-isopropylidene-6-(2-thiazolyl)-α-D-galacto-hexo-1,5-pyranose (118377-18-7)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; Yield given. Multistep reaction; 1.) THF, reflux, 20 min, 2.) room temp., overnight;

DOI:10.1021/jo00264a035

upstream raw materials:

benzyl bromide

(6S)-1,2:3,4-di-O-isopropylidene-6-(2-thiazolyl)-α-D-galacto-hexo-1,5-pyranose

(3aR,5S,5aR,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-carbaldehyde

Downstream raw materials:

6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-glycero-D-galacto-heptodialdo-1,5-pyranose

(7S)-6-O-benzyl-1,2:3,4-di-O-isopropylidene-7-(2-thiazolyl)-α-D-galacto-D-glycero-heptulo-1,5-pyranose

(1R,2R)-2-Benzyloxy-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-1-thiazol-2-yl-ethanol

6-O-benzyl-1,2:3,4-di-O-isopropylidene-α-D-galacto-D-glycero-heptodialdo-1,5-pyranose