(2S,4aR,6S,7R,8R,8aS)-6-Benzyloxy-2-methyl-8-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,4aR,6S,7R,8R,8aS)-6-Benzyloxy-2-methyl-8-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester
• CAS No.: 175876-79-6
• Molecular Formula: C₃₄H₄₂Cl₃NO₁₈
• Molecular Weight: 859.062

Synonyms:(2S,4aR,6S,7R,8R,8aS)-6-Benzyloxy-2-methyl-8-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

Chemical Property of (2S,4aR,6S,7R,8R,8aS)-6-Benzyloxy-2-methyl-8-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

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Technology Process of (2S,4aR,6S,7R,8R,8aS)-6-Benzyloxy-2-methyl-8-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

There total 5 articles about (2S,4aR,6S,7R,8R,8aS)-6-Benzyloxy-2-methyl-8-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxine-2-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: 48.0%

pyruvic acid methyl ester (600-22-6) + benzyl 2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (175876-78-5) → (2S,4aR,6S,7R,8R,8aS)-6-Benzyloxy-2-methyl-8-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester (175876-79-6)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at 25 ℃; for 2h;

DOI:10.1016/0040-4020(95)01093-9

Reference yield:

2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose (172490-46-9) → (2S,4aR,6S,7R,8R,8aS)-6-Benzyloxy-2-methyl-8-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester (175876-79-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) HCl, 2.) ZnCl₂ / 1.) 110 deg C, 2.5 h, 2.) RT, 16 h

2: 60 percent / Hg(CN)2 / benzene; nitromethane / 47 h / 60 °C

3: 98 percent / 90percent aq. AcOH / 1.5 h / 60 °C

4: 48 percent / BF₃*ether / acetonitrile / 2 h / 25 °C

With hydrogenchloride; boron trifluoride diethyl etherate; mercury(II) cyanide; acetic acid; zinc(II) chloride; In nitromethane; acetonitrile; benzene;

DOI:10.1016/0040-4020(95)01093-9

Reference yield:

benzaldehyde (100-52-7) → (2S,4aR,6S,7R,8R,8aS)-6-Benzyloxy-2-methyl-8-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester (175876-79-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) HCl, 2.) ZnCl₂ / 1.) 110 deg C, 2.5 h, 2.) RT, 16 h

2: 60 percent / Hg(CN)2 / benzene; nitromethane / 47 h / 60 °C

3: 98 percent / 90percent aq. AcOH / 1.5 h / 60 °C

4: 48 percent / BF₃*ether / acetonitrile / 2 h / 25 °C

With hydrogenchloride; boron trifluoride diethyl etherate; mercury(II) cyanide; acetic acid; zinc(II) chloride; In nitromethane; acetonitrile; benzene;

DOI:10.1016/0040-4020(95)01093-9

upstream raw materials:

pyruvic acid methyl ester

benzyl 2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

benzaldehyde

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