(1S,4aS,6S,7S,7aS)-6-Acetoxy-7-benzyloxymethyl-1-((2R,4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Base Information

• Chemical Name: (1S,4aS,6S,7S,7aS)-6-Acetoxy-7-benzyloxymethyl-1-((2R,4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester
• CAS No.: 78924-56-8
• Molecular Formula: C₄₇H₅₀O₁₂
• Molecular Weight: 806.907

Synonyms:

Chemical Property of (1S,4aS,6S,7S,7aS)-6-Acetoxy-7-benzyloxymethyl-1-((2R,4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (1S,4aS,6S,7S,7aS)-6-Acetoxy-7-benzyloxymethyl-1-((2R,4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

There total 41 articles about (1S,4aS,6S,7S,7aS)-6-Acetoxy-7-benzyloxymethyl-1-((2R,4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-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: 79.0%

(1S,4aS,6R,7S,7aS)-7-Benzyloxymethyl-1-((2R,4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-(toluene-4-sulfonyloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester (78924-55-7,78964-43-9,78964-47-3) → (1S,4aS,7S,7aS)-7-Benzyloxymethyl-1-((2R,4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-1,4a,7,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester (78924-60-4,78964-53-1) + (1S,4aS,6S,7S,7aS)-6-Acetoxy-7-benzyloxymethyl-1-((2R,4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester (78924-56-8,78964-49-5,78964-51-9,79026-77-0)

Guidance literature:

With tetraethylammonium acetate; In acetone; for 24h; Heating;

Reference yield:

tetraethylammonium acetate + (1S,4aS,6R,7S,7aS)-7-Benzyloxymethyl-1-((2R,4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-(toluene-4-sulfonyloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester (78924-55-7,78964-43-9,78964-47-3) → (1S,4aS,7S,7aS)-7-Benzyloxymethyl-1-((2R,4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-1,4a,7,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester (78924-60-4,78964-53-1) + (1S,4aS,6S,7S,7aS)-6-Acetoxy-7-benzyloxymethyl-1-((2R,4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester (78924-56-8,78964-49-5,78964-51-9,79026-77-0)

Guidance literature:

In acetone; for 24h; Heating;

Reference yield:

geniposide (24512-63-8,27745-20-6) → (1S,4aS,6R,7R,7aS)-6-Acetoxy-7-benzyloxymethyl-1-((2R,4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester (78924-56-8,78964-49-5,78964-51-9,79026-77-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 26.26 g / ZnCl₂ / Ambient temperature

2: 1.) n-Bu₄NI, NaH/DMSO / 1.) benzene, 15 min; 2.) benzene, r.t., 25 h

3: 53 percent / B₂H₆ / tetrahydrofuran

4: 622 mg / Jones reagent / acetone

5: 262 mg / NaBH₄ / dioxane; H₂O / 1 h / Ambient temperature

6: 86.3 mg / pyridine

With pyridine; sodium tetrahydroborate; jones reagent; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; zinc(II) chloride; diborane; In tetrahydrofuran; 1,4-dioxane; water; acetone;

upstream raw materials:

acetic anhydride

4',6'-O-benzylidene-2',3',10-tri-O-benzyl-7-epi-allo-10-hydroxyloganin

(1S,4aS,6S,7R,7aS)-7-Benzyloxymethyl-1-((2R,4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6-(toluene-4-sulfonyloxy)-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

geniposide

Downstream raw materials:

4',6'-O-benzylidene-2',3',10-tri-O-benzyl-10-hydroxyloganin

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