(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-4-methyl-5-(4-methylbenzyl)phenyl]-1-thio-D-glucitol

Base Information

• Chemical Name: (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-4-methyl-5-(4-methylbenzyl)phenyl]-1-thio-D-glucitol
• CAS No.: 1033723-55-5
• Molecular Formula: C₅₆H₅₆O₅S
• Molecular Weight: 841.124
• Mol file: 1033723-55-5.mol

Synonyms:(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-4-methyl-5-(4-methylbenzyl)phenyl]-1-thio-D-glucitol

Chemical Property of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-4-methyl-5-(4-methylbenzyl)phenyl]-1-thio-D-glucitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-4-methyl-5-(4-methylbenzyl)phenyl]-1-thio-D-glucitol

There total 8 articles about (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-4-methyl-5-(4-methylbenzyl)phenyl]-1-thio-D-glucitol 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: 88.0%

2,3,4,6-tetra-O-benzyl-1-C-[2-(benzyloxy)-4-methyl-5-(4-methylbenzyl)phenyl]-5-thio-D-glucopyranose → (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-4-methyl-5-(4-methylbenzyl)phenyl]-1-thio-D-glucitol (1033723-55-5)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In chloroform; acetonitrile;

Reference yield:

benzyl bromide (100-39-0) → (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-4-methyl-5-(4-methylbenzyl)phenyl]-1-thio-D-glucitol (1033723-55-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium carbonate; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 20 °C

2.1: sodium bromide; Oxone / acetone; water / 20 °C

3.1: oxalyl dichloride; N,N-dimethyl-formamide / chloroform / 20 °C

3.2: 20 °C

3.3: 0 °C

4.1: n-butyllithium / tetrahydrofuran / -78 °C

5.1: triethylsilane; boron trifluoride diethyl etherate / chloroform; acetonitrile / 0 °C

6.1: magnesium / tetrahydrofuran

7.1: triethylsilane; boron trifluoride diethyl etherate / chloroform; acetonitrile / -15 °C

With triethylsilane; Oxone; n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; potassium carbonate; magnesium; N,N-dimethyl-formamide; sodium bromide; In tetrahydrofuran; chloroform; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/j.bmcl.2018.09.035

Reference yield:

C22H21BrO2 → (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-4-methyl-5-(4-methylbenzyl)phenyl]-1-thio-D-glucitol (1033723-55-5)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylsilane; boron trifluoride diethyl etherate / chloroform; acetonitrile / 0 °C

2: magnesium / tetrahydrofuran

3: triethylsilane; boron trifluoride diethyl etherate / chloroform; acetonitrile / -15 °C

With triethylsilane; boron trifluoride diethyl etherate; magnesium; In tetrahydrofuran; chloroform; acetonitrile;

DOI:10.1016/j.bmcl.2018.09.035

upstream raw materials:

1-(benzyloxy)-2-bromo-5-methyl-4-(4-methylbenzyl)benzene

4'-hydroxy-2'methylacetophenone

4-benzyloxy-5-bromo-2-methylbenzoic acid

4-(benzyloxy)-5-bromo-2-methylbenzaldehyde

Downstream raw materials:

(1S)-1,5-anhydro-1-[4-methyl-5-(4-methylbenzyl)-2-hydroxyphenyl]-1-thio-D-glucitol