6-[(2R,3R,4R,5S,6R)-4-Acetoxy-6-benzyloxymethyl-5-hydroxy-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

Base Information

Chemical Name:6-[(2R,3R,4R,5S,6R)-4-Acetoxy-6-benzyloxymethyl-5-hydroxy-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester
CAS No.:502692-40-2
Molecular Formula:C₂₅H₃₄Cl₃NO₁₀
Molecular Weight:614.905
Hs Code.:

6-[(2R,3R,4R,5S,6R)-4-Acetoxy-6-benzyloxymethyl-5-hydroxy-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

Synonyms:6-[(2R,3R,4R,5S,6R)-4-Acetoxy-6-benzyloxymethyl-5-hydroxy-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

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Chemical Property of 6-[(2R,3R,4R,5S,6R)-4-Acetoxy-6-benzyloxymethyl-5-hydroxy-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

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Technology Process of 6-[(2R,3R,4R,5S,6R)-4-Acetoxy-6-benzyloxymethyl-5-hydroxy-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

There total 6 articles about 6-[(2R,3R,4R,5S,6R)-4-Acetoxy-6-benzyloxymethyl-5-hydroxy-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic 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: 90.0%

: 6-[(4aR,6R,7R,8R,8aS)-8-Acetoxy-2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy]-hexanoic acid methyl ester

: 502692-40-2
6-[(2R,3R,4R,5S,6R)-4-Acetoxy-6-benzyloxymethyl-5-hydroxy-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

Guidance literature:: With triethylsilane; trifluoroacetic acid; In dichloromethane; at 0 ℃;
DOI:10.1021/jo0206420

Reference yield:

: 4547-43-7
methyl 6-hydroxycaproate

: 502692-40-2
6-[(2R,3R,4R,5S,6R)-4-Acetoxy-6-benzyloxymethyl-5-hydroxy-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / molecular sieves AW-300; methyl triflate; dimethyl disulfide / CH₂Cl₂ / -20 - 0 °C

2: NaOMe; MeOH / CH₂Cl₂ / 0 °C

3: (+/-)-10-camphorsulfonic acid / acetonitrile / 20 °C

4: DMAP; pyridine / CH₂Cl₂ / 20 °C

5: 90 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 0 °C

With pyridine; methanol; triethylsilane; dmap; Dimethyldisulphide; 3 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; trifluoroacetic acid; methyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; 2: Zemplen deacetylation;
DOI:10.1021/jo0206420

Reference yield:

: 220645-20-5
p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethyloxycarbonylamino)-β-D-glucopyranoside

: 502692-40-2
6-[(2R,3R,4R,5S,6R)-4-Acetoxy-6-benzyloxymethyl-5-hydroxy-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-hexanoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 80 percent / molecular sieves AW-300; methyl triflate; dimethyl disulfide / CH₂Cl₂ / -20 - 0 °C

2: NaOMe; MeOH / CH₂Cl₂ / 0 °C

3: (+/-)-10-camphorsulfonic acid / acetonitrile / 20 °C

4: DMAP; pyridine / CH₂Cl₂ / 20 °C

5: 90 percent / triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 0 °C

With pyridine; methanol; triethylsilane; dmap; Dimethyldisulphide; 3 A molecular sieve; camphor-10-sulfonic acid; sodium methylate; trifluoroacetic acid; methyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; 2: Zemplen deacetylation;
DOI:10.1021/jo0206420