(1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-3,4,5-tris(benzyloxymethyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane

Base Information

• Chemical Name: (1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-3,4,5-tris(benzyloxymethyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane
• CAS No.: 208338-37-8
• Molecular Formula: C₄₅H₅₄O₁₀
• Molecular Weight: 754.918

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

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

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

There total 2 articles about (1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-3,4,5-tris(benzyloxymethyl)-4,6,7-trihydroxy-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: 90.0%

(4'R,5'R,1''R,2''R,3''R,4''S,5''R)-2-[4'-acetoxy-5'-methyl-6'-phenyl-hex-1'-yl]-2-[6''-benzyloxy-3'',4''-bis(benzyloxymethyl)-2'',3'',4'',5''-bis(di-O-isopropylidene)-1''-hydroxyhex-1''-yl][1,3]dithiane (208338-32-3) → (1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-3,4,5-tris(benzyloxymethyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane (208338-37-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; water; for 0.5h;

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

Reference yield: 90.0%

(4'R,5'R,1''R,2''R,3''R,4''S,5''R)-2-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-2-[6''-benzyloxy-3'',4''-bis(benzyloxymethyl)-1'',2'',4'',5''-bis(di-O-isopropylidene)-3''-hydroxyhex-1''-yl][1,3]dithiane (306281-52-7) → (1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-3,4,5-tris(benzyloxymethyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane (208338-37-8)

Guidance literature:

With water; In dichloromethane; trifluoroacetic acid; for 0.5h;

DOI:10.1021/jo000700m

Reference yield: 97.0%

benzoyl chloride (98-88-4) + (1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-3,4,5-tris(benzyloxymethyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane (208338-37-8) → (1S,3R,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-6,7-bis(benzoyloxy)-3,4,5-tris(benzyloxymethyl)-4-hydroxy-2,8-dioxabicyclo[3.2.1]octane (208338-43-6)

Guidance literature:

With pyridine; dmap;

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

upstream raw materials:

(4'R,5'R,1''R,2''R,3''R,4''S,5''R)-2-[4'-acetoxy-5'-methyl-6'-phenyl-hex-1'-yl]-2-[6''-benzyloxy-3'',4''-bis(benzyloxymethyl)-2'',3'',4'',5''-bis(di-O-isopropylidene)-1''-hydroxyhex-1''-yl][1,3]dithiane

(4'R,5'R,1''R,2''R,3''R,4''S,5''R)-2-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-2-[6''-benzyloxy-3'',4''-bis(benzyloxymethyl)-1'',2'',4'',5''-bis(di-O-isopropylidene)-3''-hydroxyhex-1''-yl][1,3]dithiane

Downstream raw materials:

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

(1S,3S,4S,5R,6R,7R,4'R,5'R)-1-[4'-acetoxy-5'-methyl-6'-phenylhex-1'-yl]-3,4,5-tris(2,2-dimethylpropionyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane

(+)-zaragozic acid

tri(tert-butyl) [1S,1(4R,5R),3S,4S,5R,6R,7R]-1-(4-acetoxy-5-methyl-6-phenylhexyl)-7-(tert-butoxycarbonyl)oxy-4,6-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate

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