(2R,4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-methoxy-8-(4-methoxy-benzyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

• Chemical Name: (2R,4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-methoxy-8-(4-methoxy-benzyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS No.: 162583-82-6
• Molecular Formula: C₃₀H₃₄O₈
• Molecular Weight: 522.595
• Mol file: 162583-82-6.mol

Synonyms:(2R,4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-methoxy-8-(4-methoxy-benzyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property of (2R,4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-methoxy-8-(4-methoxy-benzyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-methoxy-8-(4-methoxy-benzyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 5 articles about (2R,4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-methoxy-8-(4-methoxy-benzyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine 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: 87.0%

p-methoxybenzyl chloride (824-94-2) + methyl 2-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside (162583-81-5) → (2R,4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-methoxy-8-(4-methoxy-benzyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine (162583-82-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1021/ja00116a046

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (2R,4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-methoxy-8-(4-methoxy-benzyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine (162583-82-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / p-toluenesulfonic acid / dimethylformamide / 70 °C

2: 1.) n-Bu₂SnO, n-Bu₄NI, 4A molecular sieves / 1.) CH₃CN, reflux, 2 h, 2.) CH₃CN, reflux, 16 h

3: 87 percent / NaH / dimethylformamide / Ambient temperature

With 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1021/ja00116a046

Reference yield:

benzyl bromide (100-39-0) → (2R,4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-methoxy-8-(4-methoxy-benzyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine (162583-82-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-Bu₂SnO, n-Bu₄NI, 4A molecular sieves / 1.) CH₃CN, reflux, 2 h, 2.) CH₃CN, reflux, 16 h

2: 87 percent / NaH / dimethylformamide / Ambient temperature

With 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; In N,N-dimethyl-formamide;

DOI:10.1021/ja00116a046

upstream raw materials:

p-methoxybenzyl chloride

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

p-Anisaldehyde dimethyl acetal

benzyl bromide

Downstream raw materials:

methyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-glucopyranoside

(1R,2S,3S,4R,5S)-3-(benzyloxy)-4-hydroxy-1,2-bis-<(p-methoxybenzyl)oxy>-5-vinylcyclopentane

methyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hexodialdopyranoside (1,5)

methyl 2-O-benzyl-6,7-dideoxy-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hept-6-enopyranoside (1,5)