Acetic acid (4S,5S,6S)-4-benzyloxycarbonylamino-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-2-yl ester

Base Information

Chemical Name:Acetic acid (4S,5S,6S)-4-benzyloxycarbonylamino-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-2-yl ester
CAS No.:221182-43-0
Molecular Formula:C₂₅H₃₁NO₇
Molecular Weight:457.524
Hs Code.:

Synonyms:Acetic acid (4S,5S,6S)-4-benzyloxycarbonylamino-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-2-yl ester

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Chemical Property of Acetic acid (4S,5S,6S)-4-benzyloxycarbonylamino-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-2-yl ester

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Technology Process of Acetic acid (4S,5S,6S)-4-benzyloxycarbonylamino-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-2-yl ester

There total 7 articles about Acetic acid (4S,5S,6S)-4-benzyloxycarbonylamino-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-2-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: 96.0%

: 108-24-7
acetic anhydride

: [(2S,3S,4S)-6-Hydroxy-3-(4-methoxy-benzyloxy)-2,4-dimethyl-tetrahydro-pyran-4-yl]-carbamic acid benzyl ester

: 221182-43-0
Acetic acid (4S,5S,6S)-4-benzyloxycarbonylamino-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-2-yl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 23 ℃; for 2h;
DOI:10.1002/(SICI)1521-3773(19990115)38:1/2<240::AID-ANIE240>3.0.CO;2-5

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 221182-43-0
Acetic acid (4S,5S,6S)-4-benzyloxycarbonylamino-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-2-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: NaHCO₃, H₂O / dioxane / 2 h / 23 °C

2: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, -78 to 23 deg C, 6 h

3: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / 23 °C

With dmap; dimethylsulfide; water; sodium hydrogencarbonate; ozone; triethylamine; In 1,4-dioxane; dichloromethane;
DOI:10.1002/(SICI)1521-3773(19990115)38:1/2<240::AID-ANIE240>3.0.CO;2-5

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 221182-43-0
Acetic acid (4S,5S,6S)-4-benzyloxycarbonylamino-5-(4-methoxy-benzyloxy)-4,6-dimethyl-tetrahydro-pyran-2-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / NaH / tetrahydrofuran / 3 h / 0 - 23 °C

2: LiAlH₄ / diethyl ether / 18 h / Heating

3: NaHCO₃, H₂O / dioxane / 2 h / 23 °C

4: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, -78 to 23 deg C, 6 h

5: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / 23 °C

With dmap; lithium aluminium tetrahydride; dimethylsulfide; water; sodium hydride; sodium hydrogencarbonate; ozone; triethylamine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane;
DOI:10.1002/(SICI)1521-3773(19990115)38:1/2<240::AID-ANIE240>3.0.CO;2-5