{(S)-2-[(2R,3R,4R,5S,6S)-3-((2S,3R,4S,5S,6S)-3-Hydroxy-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy]-1-methyl-ethyl}-carbamic acid benzyl ester

Base Information

• Chemical Name: {(S)-2-[(2R,3R,4R,5S,6S)-3-((2S,3R,4S,5S,6S)-3-Hydroxy-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy]-1-methyl-ethyl}-carbamic acid benzyl ester
• CAS No.: 142739-19-3
• Molecular Formula: C₂₇H₄₃NO₁₁
• Molecular Weight: 557.639

Synonyms:{(S)-2-[(2R,3R,4R,5S,6S)-3-((2S,3R,4S,5S,6S)-3-Hydroxy-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy]-1-methyl-ethyl}-carbamic acid benzyl ester

Chemical Property of {(S)-2-[(2R,3R,4R,5S,6S)-3-((2S,3R,4S,5S,6S)-3-Hydroxy-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy]-1-methyl-ethyl}-carbamic acid benzyl ester

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Technology Process of {(S)-2-[(2R,3R,4R,5S,6S)-3-((2S,3R,4S,5S,6S)-3-Hydroxy-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy]-1-methyl-ethyl}-carbamic acid benzyl ester

There total 8 articles about {(S)-2-[(2R,3R,4R,5S,6S)-3-((2S,3R,4S,5S,6S)-3-Hydroxy-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy]-1-methyl-ethyl}-carbamic acid benzyl 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: 88.0%

O-(3,4-di-O-methyl-2-O-<3,4-di-O-methyl-α-L-rhamnopyranosyl>-α-L-rhamnopyranosyl)-L-alanilol (142739-23-9) → {(S)-2-[(2R,3R,4R,5S,6S)-3-((2S,3R,4S,5S,6S)-3-Hydroxy-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy]-1-methyl-ethyl}-carbamic acid benzyl ester (142739-19-3)

Guidance literature:

With sodium methylate; In methanol; for 3h;

DOI:10.1016/S0040-4020(01)88483-0

Reference yield:

methyl 3,4-di-O-methyl-α-L-rhamnopyranoside (35939-76-5) → {(S)-2-[(2R,3R,4R,5S,6S)-3-((2S,3R,4S,5S,6S)-3-Hydroxy-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy]-1-methyl-ethyl}-carbamic acid benzyl ester (142739-19-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 2.04 g / 3 N H₂SO₄ / dioxane / 6 h / Heating

2: pyridine / 8 h

3: 80 percent / tri-n-butyltin methoxide / 1,2-dichloro-ethane / 3 h / Heating

4: 85 percent / DBU / CH₂Cl₂ / 0.17 h

5: 60 percent / 4 Angstroem molecular sieves, BF₃*Et₂O / CHCl₃ / 0.5 h / -20 °C

6: 88 percent / NaOCH₃ / methanol / 3 h

With pyridine; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; sodium methylate; tributyltin methoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; methanol; dichloromethane; chloroform; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4020(01)88483-0

Reference yield:

O3,O4-dimethyl-L-6-deoxy-mannose (4348-78-1) → {(S)-2-[(2R,3R,4R,5S,6S)-3-((2S,3R,4S,5S,6S)-3-Hydroxy-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-4,5-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy]-1-methyl-ethyl}-carbamic acid benzyl ester (142739-19-3)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 8 h

2: 80 percent / tri-n-butyltin methoxide / 1,2-dichloro-ethane / 3 h / Heating

3: 85 percent / DBU / CH₂Cl₂ / 0.17 h

4: 60 percent / 4 Angstroem molecular sieves, BF₃*Et₂O / CHCl₃ / 0.5 h / -20 °C

5: 88 percent / NaOCH₃ / methanol / 3 h

With pyridine; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium methylate; tributyltin methoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; chloroform; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4020(01)88483-0

upstream raw materials:

O-(3,4-di-O-methyl-2-O-<3,4-di-O-methyl-α-L-rhamnopyranosyl>-α-L-rhamnopyranosyl)-L-alanilol

methyl 3,4-di-O-methyl-α-L-rhamnopyranoside

O³,O⁴-dimethyl-L-6-deoxy-mannose

O-(2-O-acetyl-3,4-di-O-methyl-α-L-rhamnopyranosyl)-N-carbobenzyloxy-L-alanilol

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