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

Base Information

• Chemical Name: (4aR,6S,7R,8S,8aR)-6-Methoxy-7,8-bis-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS No.: 134407-59-3
• Molecular Formula: C₃₀H₃₄O₈
• Molecular Weight: 522.595
• Mol file: 134407-59-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 1 articles about (4aR,6S,7R,8S,8aR)-6-Methoxy-7,8-bis-(4-methoxy-benzyloxy)-2-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: 75.0%

methyl 4,6-O-benzylidene-α-D-glucopyranoside (3162-96-7) + p-methoxybenzyl chloride (824-94-2) → (4aR,6S,7R,8S,8aR)-6-Methoxy-7,8-bis-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (134407-59-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 110 ℃; for 2h;

DOI:10.1016/0008-6215(91)84145-5

Reference yield:

(4aR,6S,7R,8S,8aR)-6-Methoxy-7,8-bis-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (134407-59-3) → (2R,3R,4S,5R,6S)-3-Benzyloxy-6-methoxy-4,5-bis-(4-methoxy-benzyloxy)-2-methoxymethyl-tetrahydro-pyran

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 0.17 h / Heating

2: 90 percent / methylation

With lithium aluminium tetrahydride; aluminium trichloride; In diethyl ether; dichloromethane;

DOI:10.1016/0008-6215(91)84145-5

Reference yield:

(4aR,6S,7R,8S,8aR)-6-Methoxy-7,8-bis-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (134407-59-3) → (2S,3R,4R,5R,6R)-5-Benzyloxy-2-methoxy-4-(4-methoxy-benzyloxy)-6-trityloxymethyl-tetrahydro-pyran-3-ol

Guidance literature:

Multi-step reaction with 2 steps

1: 25 percent / LiAlH₄, AlCl₃ / diethyl ether; CH₂Cl₂ / 0.17 h / Heating

2: 44 percent / pyridine

With pyridine; lithium aluminium tetrahydride; aluminium trichloride; In diethyl ether; dichloromethane;

DOI:10.1016/0008-6215(91)84145-5

upstream raw materials:

methyl 4,6-O-benzylidene-α-D-glucopyranoside

p-methoxybenzyl chloride

Downstream raw materials:

methyl 4-O-benzyl-α-D-glucopyranoside

4-O-benzyl-1,5-anhydro-D-glucitol

(2S,3R,4R,5S,6R)-5-Benzyloxy-2-methoxy-6-methoxymethyl-tetrahydro-pyran-3,4-diol

(2R,3S,4S,5R,6S)-3-Benzyloxy-2-hydroxymethyl-5,6-dimethoxy-tetrahydro-pyran-4-ol