(2S,3R,4S,4aR,6R,7R,8S,8aR)-3,4,7-Tris-benzyloxy-6-(3,4-dimethoxy-benzyloxy)-2-methoxy-8-methyl-octahydro-pyrano[3,2-b]pyran

Base Information

• Chemical Name: (2S,3R,4S,4aR,6R,7R,8S,8aR)-3,4,7-Tris-benzyloxy-6-(3,4-dimethoxy-benzyloxy)-2-methoxy-8-methyl-octahydro-pyrano[3,2-b]pyran
• CAS No.: 110045-80-2
• Molecular Formula: C₄₀H₄₆O₉
• Molecular Weight: 670.8
• Mol file: 110045-80-2.mol

Synonyms:

Chemical Property of (2S,3R,4S,4aR,6R,7R,8S,8aR)-3,4,7-Tris-benzyloxy-6-(3,4-dimethoxy-benzyloxy)-2-methoxy-8-methyl-octahydro-pyrano[3,2-b]pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,4aR,6R,7R,8S,8aR)-3,4,7-Tris-benzyloxy-6-(3,4-dimethoxy-benzyloxy)-2-methoxy-8-methyl-octahydro-pyrano[3,2-b]pyran

There total 1 articles about (2S,3R,4S,4aR,6R,7R,8S,8aR)-3,4,7-Tris-benzyloxy-6-(3,4-dimethoxy-benzyloxy)-2-methoxy-8-methyl-octahydro-pyrano[3,2-b]pyran 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:

benzyl bromide (100-39-0) + methyl-(1) 3,4-dimethoxybenzyl-(8)(8R)-2,3-di-O-benzyl-6-deoxy-6-C-methyl-β-L-threo-D-gluco-octodialdo-1,5:8,4-dipyranoside (110045-79-9) → (2S,3R,4S,4aR,6R,7R,8S,8aR)-3,4,7-Tris-benzyloxy-6-(3,4-dimethoxy-benzyloxy)-2-methoxy-8-methyl-octahydro-pyrano[3,2-b]pyran (110045-80-2)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; Yield given. Multistep reaction; 1.) DMF, 0 deg C, 20 min, 2.) DMF, RT, 45 min;

DOI:10.1021/jo00229a015

Reference yield:

(2S,3R,4S,4aR,6R,7R,8S,8aR)-3,4,7-Tris-benzyloxy-6-(3,4-dimethoxy-benzyloxy)-2-methoxy-8-methyl-octahydro-pyrano[3,2-b]pyran (110045-80-2) → methyl 4-O-acetyl-2,3,7-tri-O-benzyl-6-deoxy-6,8-di-C-methyl-L-arabino-α-D-gluco-nono-1,5-pyranoside (110046-06-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂; dioxane; H₂O / 4 h / Ambient temperature

2: pyridinium chlorochromate (PCC), Celite, Florisil, sodium acetate / CH₂Cl₂ / Ambient temperature

3: 72 percent / diethyl ether / -78 - -60 °C

4: 29 percent / tetrahydrofuran / -78 - 0 °C

5: 4-(dimethylamino)pyridine / ethyl acetate / Ambient temperature

6: 1.) O₃, 2.) Me₂S / 1.) methanol, CH₂Cl₂, RT, 0.5 , 2.) methanol, CH₂Cl₂, RT, 0.5 h

7: NaBH₄ / methanol / 0.17 h / 0 °C

With dmap; sodium tetrahydroborate; florisil; dimethylsulfide; Celite; sodium acetate; ozone; pyridinium chlorochromate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; ethyl acetate;

DOI:10.1021/jo00229a015

Reference yield:

(2S,3R,4S,4aR,6R,7R,8S,8aR)-3,4,7-Tris-benzyloxy-6-(3,4-dimethoxy-benzyloxy)-2-methoxy-8-methyl-octahydro-pyrano[3,2-b]pyran (110045-80-2) → (2R,3R,4S,4aR,6S,7R,8S,8aR)-3,7,8-Tris-benzyloxy-6-methoxy-4-methyl-octahydro-pyrano[3,2-b]pyran-2-ol

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; dichloromethane; water; for 4h; Ambient temperature;

DOI:10.1021/jo00229a015

upstream raw materials:

benzyl bromide

methyl-(1) 3,4-dimethoxybenzyl-(8)(8R)-2,3-di-O-benzyl-6-deoxy-6-C-methyl-β-L-threo-D-gluco-octodialdo-1,5:8,4-dipyranoside

Downstream raw materials:

methyl 2,3,7-tri-O-benzyl-6-deoxy-6-C-methyl-L-threo-α-D-gluco-octapyranosiduronic acid γ-lactone

methyl 2,3,7-tri-O-benzyl-6-deoxy-6-methyl-L-threo-α-D-gluco-nonpyranosid-8-ulose

methyl 4-O-acetyl-2,3,7-tri-O-benzyl-6,8,9-trideoxy-6,8-di-C-methyl-L-threo-α-D-gluco-non-8-eno-1,5-pyranoside

methyl 2,3,7-tri-O-benzyl-6,9,10-trideoxy-6,8-di-C-methyl-D-xylo-α-D-gluco-dec-9-eno-1,5-pyranoside