(1S,3R,4S,5R,6R,7R)-4,6,7-trihydroxy-3,4,5-tri-(benzyloxymethyl)-1-methyl-2,8-dioxabicyclo[3.2.1]octane

Base Information

• Chemical Name: (1S,3R,4S,5R,6R,7R)-4,6,7-trihydroxy-3,4,5-tri-(benzyloxymethyl)-1-methyl-2,8-dioxabicyclo[3.2.1]octane
• CAS No.: 172790-43-1
• Molecular Formula: C₃₁H₃₆O₈
• Molecular Weight: 536.622

Synonyms:(1S,3R,4S,5R,6R,7R)-4,6,7-trihydroxy-3,4,5-tri-(benzyloxymethyl)-1-methyl-2,8-dioxabicyclo[3.2.1]octane

Chemical Property of (1S,3R,4S,5R,6R,7R)-4,6,7-trihydroxy-3,4,5-tri-(benzyloxymethyl)-1-methyl-2,8-dioxabicyclo[3.2.1]octane

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Technology Process of (1S,3R,4S,5R,6R,7R)-4,6,7-trihydroxy-3,4,5-tri-(benzyloxymethyl)-1-methyl-2,8-dioxabicyclo[3.2.1]octane

There total 2 articles about (1S,3R,4S,5R,6R,7R)-4,6,7-trihydroxy-3,4,5-tri-(benzyloxymethyl)-1-methyl-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: 78.0%

(1'R,2'R,3'R,4'S,5'R)-2-[(2',3',4',5'-bis-(di-O-isopropylidene))-6'-benzyloxy-3',4'-bis-(benzyloxymethyl)-1'-hydroxy-hexyl]-2-methyl-1,3-dithiane (172790-42-0) → (1S,3R,4S,5R,6R,7R)-4,6,7-trihydroxy-3,4,5-tri-(benzyloxymethyl)-1-methyl-2,8-dioxabicyclo[3.2.1]octane (172790-43-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; water; for 16h; Ambient temperature;

DOI:10.1016/S0040-4039(98)00485-7

Reference yield: 47.0%

(3R,4R,5R,6S,7R)-(4,5,6,7-bis-(di-O-isopropylidene))-8-benzyloxy-5,6-bis-(benzyloxymethyl)-3-hydroxy-octan-2-one (208338-34-5) → (1S,2R,3R,4R,5S,6R)-2,3,4-trihydroxy-4,5,6-tri-(benzyloxymethyl)-1-methyl-7,8-dioxabicyclo[3.2.1]octane + (1S,3R,4S,5R,6R,7R)-4,6,7-trihydroxy-3,4,5-tri-(benzyloxymethyl)-1-methyl-2,8-dioxabicyclo[3.2.1]octane (172790-43-1)

Guidance literature:

With hydrogenchloride; methanol; at 50 ℃;

DOI:10.1016/S0040-4039(98)00485-7

Reference yield: 100.0%

benzoyl chloride (98-88-4) + (1S,3R,4S,5R,6R,7R)-4,6,7-trihydroxy-3,4,5-tri-(benzyloxymethyl)-1-methyl-2,8-dioxabicyclo[3.2.1]octane (172790-43-1) → (1S,3R,4S,5R,6R,7R)-6,7-bis-benzoyloxy-3,4,5-tris-benzyloxymethyl-4-hydroxy-1-methyl-2,8-dioxadicyclo[3.2.1]octane (306281-57-2)

Guidance literature:

With pyridine; dmap; at 20 - 50 ℃; for 8.75h;

DOI:10.1021/jo000700m

upstream raw materials:

(3R,4R,5R,6S,7R)-(4,5,6,7-bis-(di-O-isopropylidene))-8-benzyloxy-5,6-bis-(benzyloxymethyl)-3-hydroxy-octan-2-one

(1'R,2'R,3'R,4'S,5'R)-2-[(2',3',4',5'-bis-(di-O-isopropylidene))-6'-benzyloxy-3',4'-bis-(benzyloxymethyl)-1'-hydroxy-hexyl]-2-methyl-1,3-dithiane

Downstream raw materials:

(1S,3R,4S,5R,6R,7R)-6,7-bis-benzoyloxy-3,4,5-tris-benzyloxymethyl-4-hydroxy-1-methyl-2,8-dioxadicyclo[3.2.1]octane

C₂₄H₂₀O₁₀

(1S,3R,4S,5R,6R,7R)-6,7-bis-benzoyloxy-4-hydroxy-1-methyl-3,4,5-trihydroxymethyl-2,8-dioxabicyclo[3.2.1]octane

(1S,3S,4S,5R,6R,7R)-6,7-Bis-benzoyloxy-4-hydroxy-1-methyl-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

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