(4aR,6R,7R,8S,8aR)-6-[(2R,3R,4S,5R,6S)-6-((1R,2R,3S,4R,5R)-3,4-Dimethoxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-dimethoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-7,8-dimethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

• Chemical Name: (4aR,6R,7R,8S,8aR)-6-[(2R,3R,4S,5R,6S)-6-((1R,2R,3S,4R,5R)-3,4-Dimethoxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-dimethoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-7,8-dimethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS No.: 214406-27-6
• Molecular Formula: C₃₂H₄₈O₁₅
• Molecular Weight: 672.724

Synonyms:

Chemical Property of (4aR,6R,7R,8S,8aR)-6-[(2R,3R,4S,5R,6S)-6-((1R,2R,3S,4R,5R)-3,4-Dimethoxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-dimethoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-7,8-dimethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property:

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Useful:

Technology Process of (4aR,6R,7R,8S,8aR)-6-[(2R,3R,4S,5R,6S)-6-((1R,2R,3S,4R,5R)-3,4-Dimethoxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-dimethoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-7,8-dimethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 1 articles about (4aR,6R,7R,8S,8aR)-6-[(2R,3R,4S,5R,6S)-6-((1R,2R,3S,4R,5R)-3,4-Dimethoxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-dimethoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-7,8-dimethoxy-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:

(4aR,6R,7R,8R,8aS)-6-[(2R,3S,4R,5R,6S)-6-((1R,2R,3S,4R,5R)-3,4-Dimethoxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol + methyl iodide (74-88-4) → (4aR,6R,7R,8S,8aR)-6-[(2R,3R,4S,5R,6S)-6-((1R,2R,3S,4R,5R)-3,4-Dimethoxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-dimethoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-7,8-dimethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (214406-27-6)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; for 5h; Yield given; Ambient temperature;

DOI:10.1016/S0960-894X(98)00382-5

Reference yield:

(4aR,6R,7R,8S,8aR)-6-[(2R,3R,4S,5R,6S)-6-((1R,2R,3S,4R,5R)-3,4-Dimethoxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-dimethoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-7,8-dimethoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (214406-27-6) → Benzoic acid (2R,3R,4S,5R,6R)-6-[(2R,3R,4S,5R,6S)-6-((1R,2R,3S,4R,5R)-3,4-dimethoxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-4,5-dimethoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / 80percent AcOH / 6 h / 50 °C

2: 91 percent / Et₃N / CH₂Cl₂ / 15 h / Ambient temperature

With acetic acid; triethylamine; In dichloromethane;

DOI:10.1016/S0960-894X(98)00382-5

upstream raw materials:

methyl iodide

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