Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-methoxymethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-2-[(2S,3R,4S,5S,6R)-3,4,5-tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-thiopyran-2-yloxymethyl]-tetrahydro-thiopyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-methoxymethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-2-[(2S,3R,4S,5S,6R)-3,4,5-tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-thiopyran-2-yloxymethyl]-tetrahydro-thiopyran-3-yl ester
CAS No.:838853-71-7
Molecular Formula:C₅₂H₆₂Cl₃NO₁₆S₂
Molecular Weight:1127.55
Hs Code.:

Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-methoxymethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-2-[(2S,3R,4S,5S,6R)-3,4,5-tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-thiopyran-2-yloxymethyl]-tetrahydro-thiopyran-3-yl ester

Synonyms:Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-methoxymethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-2-[(2S,3R,4S,5S,6R)-3,4,5-tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-thiopyran-2-yloxymethyl]-tetrahydro-thiopyran-3-yl ester

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Chemical Property of Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-methoxymethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-2-[(2S,3R,4S,5S,6R)-3,4,5-tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-thiopyran-2-yloxymethyl]-tetrahydro-thiopyran-3-yl ester

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Technology Process of Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-methoxymethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-2-[(2S,3R,4S,5S,6R)-3,4,5-tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-thiopyran-2-yloxymethyl]-tetrahydro-thiopyran-3-yl ester

There total 9 articles about Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-methoxymethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-2-[(2S,3R,4S,5S,6R)-3,4,5-tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-thiopyran-2-yloxymethyl]-tetrahydro-thiopyran-3-yl 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: 77.0%

: 545-06-2
trichloroacetonitrile

: 756485-50-4
3,4-O-diacetoxy-5-deoxy-6-O-[5'-deoxy-2',3',4',6'-O-tetrakis(4-methoxyphenylmethyl)-5'-thio-α-D-glucopyranosyl]-2-O-methoxymethyl-5-thio-α-D-glucopyranose

: 838853-71-7
Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-methoxymethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-2-[(2S,3R,4S,5S,6R)-3,4,5-tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-thiopyran-2-yloxymethyl]-tetrahydro-thiopyran-3-yl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 - 20 ℃;
DOI:10.1016/j.tet.2004.06.006

Reference yield:

: 592517-48-1
6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-5-thio-D-glucopyranose

: 838853-71-7
Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-methoxymethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-2-[(2S,3R,4S,5S,6R)-3,4,5-tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-thiopyran-2-yloxymethyl]-tetrahydro-thiopyran-3-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 86 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / 20 °C

2: 43 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / -20 °C

3: 100 percent / NaOMe / methanol / 20 h / 20 °C

4: 93 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 2 h / -78 - 20 °C

5: 51 percent / pyridine; trifluoroacetic anhydride / CH₂Cl₂ / 0 °C

6: 61 percent / aq. HCl / methanol / 1 h / 20 °C

7: pyridine / CH₂Cl₂ / 33 h / 20 °C

8: 79 percent / hydrazine acetate / dimethylformamide / 12 h / 20 °C

9: 77 percent / DBU / CH₂Cl₂ / 0 - 20 °C

With pyridine; hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In methanol; dichloromethane; N,N-dimethyl-formamide; 5: Pummerer rearrangement;
DOI:10.1016/j.tet.2004.06.006

Reference yield:

: 592517-52-7
6-O-benzoyl-1,5-dideoxy-3,4-O-isopropylidene-2-O-methoxymethyl-5-thio-D-glucopyranose

: 838853-71-7
Acetic acid (2R,3S,4S,5R,6S)-4-acetoxy-5-methoxymethoxy-6-(2,2,2-trichloro-acetimidoyloxy)-2-[(2S,3R,4S,5S,6R)-3,4,5-tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-thiopyran-2-yloxymethyl]-tetrahydro-thiopyran-3-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 43 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 0.5 h / -20 °C

2: 100 percent / NaOMe / methanol / 20 h / 20 °C

3: 93 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂ / 2 h / -78 - 20 °C

4: 51 percent / pyridine; trifluoroacetic anhydride / CH₂Cl₂ / 0 °C

5: 61 percent / aq. HCl / methanol / 1 h / 20 °C

6: pyridine / CH₂Cl₂ / 33 h / 20 °C

7: 79 percent / hydrazine acetate / dimethylformamide / 12 h / 20 °C

8: 77 percent / DBU / CH₂Cl₂ / 0 - 20 °C

With pyridine; hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium methylate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In methanol; dichloromethane; N,N-dimethyl-formamide; 4: Pummerer rearrangement;
DOI:10.1016/j.tet.2004.06.006