[(3S,6R)-6-(Benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(3S,6R)-6-(Benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester
• CAS No.: 75466-93-2
• Molecular Formula: C₂₂H₂₄N₂O₆
• Molecular Weight: 412.442

Synonyms:[(3S,6R)-6-(Benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Chemical Property of [(3S,6R)-6-(Benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

Chemical Property:

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Technology Process of [(3S,6R)-6-(Benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester

There total 18 articles about [(3S,6R)-6-(Benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-yl]-carbamic acid benzyl 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: 39.0%

dicarbobenzoxy-δ-hydroxy-L-lysine-lactone (96261-29-9) → Dicarbobenzoxy-allohydroxylysin-δ-lacton (86235-37-2) + [(3S,6R)-6-(Benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (75466-93-2)

Guidance literature:

In chloroform; acetone; column separation;

DOI:10.1016/S0040-4020(01)98942-2

Reference yield:

tert-butyl (S)-4-(but-3-enyl)-2,2-dimethyloxazolidine-3-carboxylate (144090-57-3) → [(3S,6R)-6-(Benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (75466-93-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / m-chloroperbenzoic acid (mCPBA) / 1,2-dichloro-ethane; H₂O / 50 °C / pH 8

2: 48 percent / NaN₃, NH₄Cl / 2-methoxy-ethanol; H₂O / 50 °C

3: 97 percent / NaH, n-Bu₄NI / tetrahydrofuran / Ambient temperature

4: TsOH / methanol / Ambient temperature

5: CrO₃, dil. H₂SO₄ / acetone / 0 °C

6: H₂, dil. HCl / 20percent Pd(OH)2 / ethanol

7: aq. NaOH / ethanol; tetrahydrofuran

8: TFA / CH₂Cl₂

9: aq. NaOH / ethanol; tetrahydrofuran

10: toluene / Heating

With chromium(VI) oxide; hydrogenchloride; sodium hydroxide; sodium azide; sulfuric acid; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; 2-methoxy-ethanol; water; 1,2-dichloro-ethane; acetone; toluene;

DOI:10.1039/c39920001064

Reference yield:

(S)-2,2-Dimethyl-4-(2-oxiranyl-ethyl)-oxazolidine-3-carboxylic acid tert-butyl ester (144090-58-4,144090-70-0) → [(3S,6R)-6-(Benzyloxycarbonylamino-methyl)-2-oxo-tetrahydro-pyran-3-yl]-carbamic acid benzyl ester (75466-93-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 48 percent / NaN₃, NH₄Cl / 2-methoxy-ethanol; H₂O / 50 °C

2: 97 percent / NaH, n-Bu₄NI / tetrahydrofuran / Ambient temperature

3: TsOH / methanol / Ambient temperature

4: CrO₃, dil. H₂SO₄ / acetone / 0 °C

5: H₂, dil. HCl / 20percent Pd(OH)2 / ethanol

6: aq. NaOH / ethanol; tetrahydrofuran

7: TFA / CH₂Cl₂

8: aq. NaOH / ethanol; tetrahydrofuran

9: toluene / Heating

With chromium(VI) oxide; hydrogenchloride; sodium hydroxide; sodium azide; sulfuric acid; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; ammonium chloride; toluene-4-sulfonic acid; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; 2-methoxy-ethanol; water; acetone; toluene;

DOI:10.1039/c39920001064

upstream raw materials:

dicarbobenzoxy-δ-hydroxy-L-lysine-lactone

(2S,5R)-2-amino-6-[(benzyloxycarbonyl)amino]-5-hydroxyhexanoic acid

benzyl chloroformate

tert-butyl (S)-4-(but-3-enyl)-2,2-dimethyloxazolidine-3-carboxylate

Downstream raw materials:

(+/-)-N-(threo-2,6-bis-benzyloxycarbonylamino-5-hydroxy-hexanoyl)-glycine amide

optically inactive N-((2Ξ)-threo-2,6-bis-benzyloxycarbonylamino-5-hydroxy-hexanoyl)-Ξ-alanine amide

D-glycero-D-guloheptonic acid

(+/-)-threo-2,6-bis-benzyloxycarbonylamino-5-hydroxy-hexanoic acid amide

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