methyl 2--2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2--2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside
• CAS No.: 141438-52-0
• Molecular Formula: C₂₃H₂₇NO₈
• Molecular Weight: 445.469
• Mol file: 141438-52-0.mol

Synonyms:methyl 2--2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside

Chemical Property of methyl 2--2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2--2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside

There total 3 articles about methyl 2--2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside 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: 75.0%

p-Anisaldehyde dimethyl acetal (2186-92-7) + ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester (4704-15-8) → methyl 2--2-deoxy-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside (141438-52-0)

Guidance literature:

With camphor-10-sulfonic acid; In N,N-dimethyl-formamide; at 90 ℃; for 4h;

DOI:10.1021/jo00039a044

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) + ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester (4704-15-8) → [(2R,4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester (141438-52-0)

Guidance literature:

With camphor-10-sulfonic acid; In N,N-dimethyl-formamide; at 80 ℃; Yield given;

DOI:10.1021/jo00048a006

Reference yield:

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose (3006-58-4,13030-01-8,42890-10-8,42973-23-9,77059-32-6,121785-09-9,7474-40-0) → [(2R,4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-carbamic acid benzyl ester (141438-52-0)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / 24 h / Heating

2: CSA / dimethylformamide / 80 °C

With hydrogenchloride; camphor-10-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jo00048a006

upstream raw materials:

p-Anisaldehyde dimethyl acetal

((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

2-carbobenzyloxyamino-2-deoxy-D-glucopyranose

Downstream raw materials:

(2E,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate

(2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-3-bromo-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate

(2Z,4R,5R) methyl 4-acetoxy-5-[(2S)-N-(benzoxycarbonyl)aziridin-2-yl]-5-[(tert-butyldimethylsilyl)oxy]-2-[N-(methoxycarbonyl)amino]-2-pentenoate

(S)-2-[(E)-(1R,2R)-2-Acetoxy-1-(tert-butyl-dimethyl-silanyloxy)-4-methoxycarbonyl-4-methoxycarbonylamino-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester