(R)-3-[(2R,3R,4aS,5S,7R,8R,8aR)-2,3-Dimethoxy-2,3,5-trimethyl-8-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,4-b][1,4]dioxin-7-yloxy]-decanoic acid 2-oxo-2-phenyl-ethyl ester

Base Information

• Chemical Name: (R)-3-[(2R,3R,4aS,5S,7R,8R,8aR)-2,3-Dimethoxy-2,3,5-trimethyl-8-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,4-b][1,4]dioxin-7-yloxy]-decanoic acid 2-oxo-2-phenyl-ethyl ester
• CAS No.: 202824-33-7
• Molecular Formula: C₅₇H₇₄O₁₄
• Molecular Weight: 983.206

Synonyms:(R)-3-[(2R,3R,4aS,5S,7R,8R,8aR)-2,3-Dimethoxy-2,3,5-trimethyl-8-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,4-b][1,4]dioxin-7-yloxy]-decanoic acid 2-oxo-2-phenyl-ethyl ester

Chemical Property of (R)-3-[(2R,3R,4aS,5S,7R,8R,8aR)-2,3-Dimethoxy-2,3,5-trimethyl-8-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,4-b][1,4]dioxin-7-yloxy]-decanoic acid 2-oxo-2-phenyl-ethyl ester

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Technology Process of (R)-3-[(2R,3R,4aS,5S,7R,8R,8aR)-2,3-Dimethoxy-2,3,5-trimethyl-8-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,4-b][1,4]dioxin-7-yloxy]-decanoic acid 2-oxo-2-phenyl-ethyl ester

There total 7 articles about (R)-3-[(2R,3R,4aS,5S,7R,8R,8aR)-2,3-Dimethoxy-2,3,5-trimethyl-8-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,4-b][1,4]dioxin-7-yloxy]-decanoic acid 2-oxo-2-phenyl-ethyl 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:

phrnacyl (R)-3-hydroxydecanoate (119471-50-0) + (2R,3R,4aS,5S,7S,8R,8aR)-2,3-Dimethoxy-2,3,5-trimethyl-7-phenylsulfanyl-8-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,4-b][1,4]dioxine → (R)-3-[(2R,3R,4aS,5S,7R,8R,8aR)-2,3-Dimethoxy-2,3,5-trimethyl-8-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,4-b][1,4]dioxin-7-yloxy]-decanoic acid 2-oxo-2-phenyl-ethyl ester (202824-33-7)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In 1,2-dichloro-ethane; at 0 ℃; for 0.166667h; Yield given;

DOI:10.1002/(sici)1099-0690(199802)1998:2<303::aid-ejoc303>3.0.co;2-u

Reference yield:

ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamanopyranoside (128962-63-0,116391-11-8) → (R)-3-[(2R,3R,4aS,5S,7R,8R,8aR)-2,3-Dimethoxy-2,3,5-trimethyl-8-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,4-b][1,4]dioxin-7-yloxy]-decanoic acid 2-oxo-2-phenyl-ethyl ester (202824-33-7)

Guidance literature:

Multi-step reaction with 2 steps

1: N-iodosuccinimide, triflic acid

2: N-iodosuccinimide, triflic acid

With N-iodo-succinimide; trifluorormethanesulfonic acid;

DOI:10.1002/(sici)1099-0690(199802)1998:2<303::aid-ejoc303>3.0.co;2-u

Reference yield:

phenyl 1-thio-α-L-rhamnopyranose (1214-98-8,105026-40-2,127061-11-4,131724-82-8) → (R)-3-[(2R,3R,4aS,5S,7R,8R,8aR)-2,3-Dimethoxy-2,3,5-trimethyl-8-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-pyrano[3,4-b][1,4]dioxin-7-yloxy]-decanoic acid 2-oxo-2-phenyl-ethyl ester (202824-33-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / camphersulfonic acid / methanol / 18 h / Heating

2: molecular sieves 4 Angstroem, N-iodosuccinimide, triflic acid / 1,2-dichloro-ethane / 0.08 h / 0 °C

3: N-iodosuccinimide, triflic acid / 1,2-dichloro-ethane / 0.17 h / 0 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; camphor-10-sulfonic acid; In methanol; 1,2-dichloro-ethane;

DOI:10.1002/(sici)1099-0690(199802)1998:2<303::aid-ejoc303>3.0.co;2-u

upstream raw materials:

phrnacyl (R)-3-hydroxydecanoate

ethyl 2,3,4-tri-O-benzyl-1-thio-α-L-rhamanopyranoside

phenyl 1-thio-α-L-rhamnopyranose

ethyl 1-thio-α-L-rhamnopyranoside

Downstream raw materials:

rhamnolipid

(R)-3-[2-O-(2',3',4'-tri-O-benzyl-α-L-rhamnopyranosyl)-3,4-O-(2,3-dimethoxybutane-2,3-diyl)-α-L-rhamnopyranosyl]oxydecanoic acid

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