9-[(2R,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

Base Information

• Chemical Name: 9-[(2R,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester
• CAS No.: 180074-72-0
• Molecular Formula: C₅₇H₇₀O₁₂
• Molecular Weight: 947.176

Synonyms:9-[(2R,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

Chemical Property of 9-[(2R,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

Chemical Property:

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Technology Process of 9-[(2R,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester

There total 9 articles about 9-[(2R,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic 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: 70.0%

9-[(4aR,6R,7R,8S,8aR)-7-Benzyloxy-2-phenyl-8-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-nonanoic acid methyl ester → 9-[(2R,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester (180074-72-0)

Guidance literature:

With hydrogenchloride; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether;

DOI:10.1016/0960-894X(96)00240-5

Reference yield:

methyl 9-hydroxynonanoate (34957-73-8) → 9-[(2R,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester (180074-72-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / Ag₂O, AgOTf / CH₂Cl₂

2: NaOMe / methanol

3: 85 percent / p-TsOH / acetonitrile

4: 70 percent / Drierite / CH₂Cl₂; pyridine / -50 °C

5: 72 percent / Ag₂O / CH₂Cl₂

6: NaOMe / methanol

7: 82 percent / CuBr₂, TEABr, mol. sieve / dimethylformamide; CH₂Cl₂

8: 70 percent / NaBH₃CN, HCl / tetrahydrofuran; diethyl ether

With hydrogenchloride; calcium sulfate; molecular sieve; tetraethylammonium bromide; sodium methylate; silver trifluoromethanesulfonate; sodium cyanoborohydride; toluene-4-sulfonic acid; copper(ll) bromide; silver(l) oxide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0960-894X(96)00240-5

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 9-[(2R,3R,4S,5R,6R)-3-Benzyloxy-6-benzyloxymethyl-5-hydroxy-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-nonanoic acid methyl ester (180074-72-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / p-TsOH / acetonitrile

2: 70 percent / Drierite / CH₂Cl₂; pyridine / -50 °C

3: 72 percent / Ag₂O / CH₂Cl₂

4: NaOMe / methanol

5: 82 percent / CuBr₂, TEABr, mol. sieve / dimethylformamide; CH₂Cl₂

6: 70 percent / NaBH₃CN, HCl / tetrahydrofuran; diethyl ether

With hydrogenchloride; calcium sulfate; molecular sieve; tetraethylammonium bromide; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; copper(ll) bromide; silver(l) oxide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0960-894X(96)00240-5

upstream raw materials:

methyl 9-hydroxynonanoate

benzaldehyde dimethyl acetal

8-(methoxycarbonyl)octyl β-D-glucopyranoside

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

C₇₁H₈₈O₂₁

C₆₃H₈₀O₁₇

C₇₀H₈₄O₁₇

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