(4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-isopropoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carboxylic acid methyl ester

Base Information

• Chemical Name: (4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-isopropoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carboxylic acid methyl ester
• CAS No.: 753502-46-4
• Molecular Formula: C₂₇H₄₄O₈Si
• Molecular Weight: 524.727
• Mol file: 753502-46-4.mol

Synonyms:(4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-isopropoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carboxylic acid methyl ester

Chemical Property of (4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-isopropoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-isopropoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carboxylic acid methyl ester

There total 1 articles about (4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-isopropoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carboxylic acid methyl ester 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:

methyl iodide (74-88-4) + (4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-isopropoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carboxylic acid → (4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-isopropoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carboxylic acid methyl ester (753502-46-4)

Guidance literature:

With potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1016/j.tet.2004.06.009

Reference yield: 90.0%

(4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-isopropoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carboxylic acid methyl ester (753502-46-4) → isopropyl 3-O-benzyl-4,6-O-benzylidene-2-O,5-C-carbonyl-β-D-glucopyranoside (753502-47-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2004.06.009

Reference yield:

(4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-isopropoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carboxylic acid methyl ester (753502-46-4) → (1R,4R,6R,7S,8S)-7-Benzyloxy-8-hydroxy-4-hydroxymethyl-6-isopropoxy-2,5-dioxa-bicyclo[2.2.2]octan-3-one

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

2: AcOH / H₂O / 3.5 h / 60 °C

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; water;

DOI:10.1016/j.tet.2004.06.009

upstream raw materials:

methyl iodide

Downstream raw materials:

isopropyl 3-O-benzyl-4,6-O-benzylidene-2-O,5-C-carbonyl-β-D-glucopyranoside