(1S,3R,4R,5S,6R,7R)-7-acetoxy-6-benzyloxy-5-benzyloxymethyl-4-benzyloxy-3-acetoxymethyl-2,8-dioxabicyclo[3.2.1]octane

Base Information

Chemical Name:(1S,3R,4R,5S,6R,7R)-7-acetoxy-6-benzyloxy-5-benzyloxymethyl-4-benzyloxy-3-acetoxymethyl-2,8-dioxabicyclo[3.2.1]octane
CAS No.:217325-03-6
Molecular Formula:C₃₃H₃₆O₉
Molecular Weight:576.643
Hs Code.:

Synonyms:(1S,3R,4R,5S,6R,7R)-7-acetoxy-6-benzyloxy-5-benzyloxymethyl-4-benzyloxy-3-acetoxymethyl-2,8-dioxabicyclo[3.2.1]octane

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Chemical Property of (1S,3R,4R,5S,6R,7R)-7-acetoxy-6-benzyloxy-5-benzyloxymethyl-4-benzyloxy-3-acetoxymethyl-2,8-dioxabicyclo[3.2.1]octane

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Technology Process of (1S,3R,4R,5S,6R,7R)-7-acetoxy-6-benzyloxy-5-benzyloxymethyl-4-benzyloxy-3-acetoxymethyl-2,8-dioxabicyclo[3.2.1]octane

There total 9 articles about (1S,3R,4R,5S,6R,7R)-7-acetoxy-6-benzyloxy-5-benzyloxymethyl-4-benzyloxy-3-acetoxymethyl-2,8-dioxabicyclo[3.2.1]octane 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: 57.0%

: 108-24-7
acetic anhydride

: 250584-41-9
(6R)-methyl-3-O-benzyl-2-O-methoxymethyl-4-C-benzyloxymethyl-6,7-O-isopropyl-α-D-galactofuranoside

: 217325-03-6
(1S,3R,4R,5S,6R,7R)-7-acetoxy-6-benzyloxy-5-benzyloxymethyl-4-benzyloxy-3-acetoxymethyl-2,8-dioxabicyclo[3.2.1]octane

: (1S,4R,5R,6S,7R,8R)-8-acetoxy-7-benzyloxy-6-benzyloxymethyl-5-benzyloxy-4-acetoxy-2,9-dioxabicyclo[4.2.1]nonane

Guidance literature:: (6R)-methyl-3-O-benzyl-2-O-methoxymethyl-4-C-benzyloxymethyl-6,7-O-isopropyl-α-D-galactofuranoside; With Dowex 50W; In acetonitrile; for 20h; Heating;

acetic anhydride; With dmap; at 20 ℃; for 1.5h;
DOI:10.1016/S0040-4020(99)00637-7

Reference yield:

: 217324-99-7
methyl (methyl-3-O-benzyl-2-O-methoxymethyl-α-D-xylofuranoside) uronate

: 217325-03-6
(1S,3R,4R,5S,6R,7R)-7-acetoxy-6-benzyloxy-5-benzyloxymethyl-4-benzyloxy-3-acetoxymethyl-2,8-dioxabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 66 percent / KHMDS; CeCl₃ / toluene; tetrahydrofuran / -100 - -20 °C

2.1: 68 percent / LiAlH₄ / diethyl ether / 2 h / 20 °C

3.1: NaH / dimethylformamide / 1.5 h / 0 - 20 °C

4.1: Dowex 50W / acetonitrile / 20 h / Heating

4.2: 57 percent / DMAP / 1.5 h / 20 °C

With lithium aluminium tetrahydride; cerium(III) chloride; Dowex 50W; potassium hexamethylsilazane; sodium hydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Condensation / 2.1: Reduction / 3.1: Alkylation / 4.1: Hydrolysis / 4.2: Acetylation;
DOI:10.1016/S0040-4020(99)00637-7

Reference yield:

: 250584-40-8
(6R)-methyl-3-O-benzyl-2-O-methoxymethyl-4-C-hydroxymethyl-6,7-O-isopropyl-α-D-galacto/α-D-gluco/β-L-altrofuranoside

: 217325-03-6
(1S,3R,4R,5S,6R,7R)-7-acetoxy-6-benzyloxy-5-benzyloxymethyl-4-benzyloxy-3-acetoxymethyl-2,8-dioxabicyclo[3.2.1]octane

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / 1.5 h / 0 - 20 °C

2.1: Dowex 50W / acetonitrile / 20 h / Heating

2.2: 57 percent / DMAP / 1.5 h / 20 °C

With Dowex 50W; sodium hydride; In N,N-dimethyl-formamide; acetonitrile; 1.1: Alkylation / 2.1: Hydrolysis / 2.2: Acetylation;
DOI:10.1016/S0040-4020(99)00637-7