Acetic acid (2R,3R,4S,5R,6S)-6-[(2R,3S,4S,5R,6S)-3-acetoxy-2-methyl-6-(naphthalen-2-yloxy)-5-phenylselanyl-tetrahydro-pyran-4-yloxy]-4-(tert-butyl-dimethyl-silanyloxy)-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4S,5R,6S)-6-[(2R,3S,4S,5R,6S)-3-acetoxy-2-methyl-6-(naphthalen-2-yloxy)-5-phenylselanyl-tetrahydro-pyran-4-yloxy]-4-(tert-butyl-dimethyl-silanyloxy)-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester
CAS No.:154367-79-0
Molecular Formula:C₅₁H₆₀O₁₂S₂SeSi
Molecular Weight:1036.21
Hs Code.:

Acetic acid (2R,3R,4S,5R,6S)-6-[(2R,3S,4S,5R,6S)-3-acetoxy-2-methyl-6-(naphthalen-2-yloxy)-5-phenylselanyl-tetrahydro-pyran-4-yloxy]-4-(tert-butyl-dimethyl-silanyloxy)-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Synonyms:Acetic acid (2R,3R,4S,5R,6S)-6-[(2R,3S,4S,5R,6S)-3-acetoxy-2-methyl-6-(naphthalen-2-yloxy)-5-phenylselanyl-tetrahydro-pyran-4-yloxy]-4-(tert-butyl-dimethyl-silanyloxy)-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2R,3R,4S,5R,6S)-6-[(2R,3S,4S,5R,6S)-3-acetoxy-2-methyl-6-(naphthalen-2-yloxy)-5-phenylselanyl-tetrahydro-pyran-4-yloxy]-4-(tert-butyl-dimethyl-silanyloxy)-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5R,6S)-6-[(2R,3S,4S,5R,6S)-3-acetoxy-2-methyl-6-(naphthalen-2-yloxy)-5-phenylselanyl-tetrahydro-pyran-4-yloxy]-4-(tert-butyl-dimethyl-silanyloxy)-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

There total 9 articles about Acetic acid (2R,3R,4S,5R,6S)-6-[(2R,3S,4S,5R,6S)-3-acetoxy-2-methyl-6-(naphthalen-2-yloxy)-5-phenylselanyl-tetrahydro-pyran-4-yloxy]-4-(tert-butyl-dimethyl-silanyloxy)-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-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: 74.0%

: 154367-78-9
Acetic acid (2R,3R,4S,5R,6S)-6-((2R,3S,4S,5R,6S)-3-acetoxy-6-hydroxy-2-methyl-5-phenylselanyl-tetrahydro-pyran-4-yloxy)-4-(tert-butyl-dimethyl-silanyloxy)-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

: 135-19-3
β-naphthol

: 154367-79-0
Acetic acid (2R,3R,4S,5R,6S)-6-[(2R,3S,4S,5R,6S)-3-acetoxy-2-methyl-6-(naphthalen-2-yloxy)-5-phenylselanyl-tetrahydro-pyran-4-yloxy]-4-(tert-butyl-dimethyl-silanyloxy)-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In toluene; at 0 ℃;
DOI:10.1016/S0040-4039(00)91806-9

Reference yield:

: 5707-04-0
Phenylselenyl chloride

: 154367-79-0
Acetic acid (2R,3R,4S,5R,6S)-6-[(2R,3S,4S,5R,6S)-3-acetoxy-2-methyl-6-(naphthalen-2-yloxy)-5-phenylselanyl-tetrahydro-pyran-4-yloxy]-4-(tert-butyl-dimethyl-silanyloxy)-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1) CH₂Cl₂, 0 deg C, 2) THF

2: 88 percent / HF*pyridine / tetrahydrofuran

3: mol. sieves 4A / TMS-OTf / CH₂Cl₂ / -78 °C

4: 81 percent / NH₂NH₂ / methanol

5: 74 percent / PPh₃, EtOOC-N=N-COOEt / toluene / 0 °C

With 4 A molecular sieve; pyridine hydrogenfluoride; triphenylphosphine; hydrazine; diethylazodicarboxylate; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1016/S0040-4039(00)91806-9

Reference yield:

: 134355-03-6
6-deoxy-D-glucal

: 154367-79-0
Acetic acid (2R,3R,4S,5R,6S)-6-[(2R,3S,4S,5R,6S)-3-acetoxy-2-methyl-6-(naphthalen-2-yloxy)-5-phenylselanyl-tetrahydro-pyran-4-yloxy]-4-(tert-butyl-dimethyl-silanyloxy)-5-phenylsulfanyl-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: Et₃N / dimethylformamide

2: Et₃N, DMAP / CH₂Cl₂

3: 1) CH₂Cl₂, 0 deg C, 2) THF

4: 88 percent / HF*pyridine / tetrahydrofuran

5: mol. sieves 4A / TMS-OTf / CH₂Cl₂ / -78 °C

6: 81 percent / NH₂NH₂ / methanol

7: 74 percent / PPh₃, EtOOC-N=N-COOEt / toluene / 0 °C

With dmap; 4 A molecular sieve; pyridine hydrogenfluoride; triethylamine; triphenylphosphine; hydrazine; diethylazodicarboxylate; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4039(00)91806-9