methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-α-D-threo-D-galacto-octopyranoside

Base Information

• Chemical Name: methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-α-D-threo-D-galacto-octopyranoside
• CAS No.: 124780-55-8
• Molecular Formula: C₂₃H₂₈O₆
• Molecular Weight: 400.472
• Mol file: 124780-55-8.mol

Synonyms:methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-α-D-threo-D-galacto-octopyranoside

Chemical Property of methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-α-D-threo-D-galacto-octopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-α-D-threo-D-galacto-octopyranoside

There total 8 articles about methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-α-D-threo-D-galacto-octopyranoside 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: 77.0%

methyl 6,7-anhydro-2,3-di-O-benzyl-4-O-carbamoyl-8-deoxy-α-D-threo-D-galacto-octoside (131751-01-4) → methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-α-D-threo-D-galacto-octopyranoside (124780-55-8)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; for 2h; Heating;

DOI:10.1071/CH9901657

Reference yield:

benzyl bromide (100-39-0) → (2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-((2R,3R)-3-methyl-oxiranyl)-tetrahydro-pyran-3-ol (124780-55-8)

Guidance literature:

Multi-step reaction with 3 steps

1: n-Bu₂SnO, n-Bu₄NI / benzene / Heating

2: pyridine / Ambient temperature

With pyridine; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; In benzene;

DOI:10.1021/jo00292a044

Reference yield:

Benzoic acid (1R,2S)-1-((2S,3R,4S,5R,6S)-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-2-bromo-propyl ester (131750-89-5) → methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-α-D-threo-D-galacto-octopyranoside (124780-55-8)

Guidance literature:

With potassium hydroxide; In methanol; for 24h; Yield given;

DOI:10.1071/CH9901657

upstream raw materials:

methyl (E)-4-O-benzoyl-2,3-di-O-benzyl-6,7,8-trideoxy-α-D-galacto-oct-6-enoside

methyl (E)-2,3-di-O-benzyl-6,7,8-trideoxy-α-D-galacto-oct-6-enopyranoside

benzyl bromide

methyl 6,7-anhydro-2,3-di-O-benzyl-4-O-carbamoyl-8-deoxy-α-D-threo-D-galacto-octoside

Downstream raw materials:

Methyl 2,3-Bis-O-(phenylmethyl)-6,8-dideoxy-7,6-<2-(N,N-dimethylamino)-1-oxa-3-azaprop-2-eno>-D-erythro-α-D-galacto-octopyranoside

methyl 4,7-anhydro-2,3-di-O-benzyl-8-deoxy-β-L-erythro-D-galacto-octoside

Trichloro-acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-((2S,3R)-3-methyl-oxiranyl)-tetrahydro-pyran-3-yl ester

methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-4-O-methyl-α-D-threo-D-galacto-octoside