(2S,3aR,6S,7R,7aR)-6-Benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-(tert-butoxycarbonyl-methyl-amino)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3aR,6S,7R,7aR)-6-Benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-(tert-butoxycarbonyl-methyl-amino)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester
CAS No.:289505-54-0
Molecular Formula:C₃₁H₄₆N₂O₁₁
Molecular Weight:622.713
Hs Code.:

(2S,3aR,6S,7R,7aR)-6-Benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-(tert-butoxycarbonyl-methyl-amino)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

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Chemical Property of (2S,3aR,6S,7R,7aR)-6-Benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-(tert-butoxycarbonyl-methyl-amino)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

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Technology Process of (2S,3aR,6S,7R,7aR)-6-Benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-(tert-butoxycarbonyl-methyl-amino)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

There total 24 articles about (2S,3aR,6S,7R,7aR)-6-Benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-(tert-butoxycarbonyl-methyl-amino)-hexahydro-furo[3,2-b]pyran-2-carboxylic 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:

: ((2R,4R,5S)-5-Benzyloxy-3-oxo-2-prop-2-ynyl-tetrahydro-pyran-4-yl)-methyl-carbamic acid tert-butyl ester

: 289505-54-0
(2S,3aR,6S,7R,7aR)-6-Benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-(tert-butoxycarbonyl-methyl-amino)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: NaBH₄ / tetrahydrofuran; methanol / -78 - 0 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

3.1: B-iodo-9-BBN / pentane / -20 °C

3.2: AcOH / pentane

4.1: PdCl₂(PPh₃)2 / tetrahydrofuran; N,N-dimethyl-acetamide / 35 °C

5.1: Bu₄NF / tetrahydrofuran / 20 °C

6.1: Et₃N / CH₂Cl₂ / 20 °C

7.1: 92 percent / m-chloroperbenzoic acid / CH₂Cl₂; aq. phosphate buffer / 20 °C / pH 7.0

8.1: camphorsulfonic acid / CH₂Cl₂ / 20 °C

9.1: 1N NaOH / tetrahydrofuran / 20 °C

10.1: tetrapropylammonium perrutenate; 4-methylmorpholine N-oxide; 4 Angstroem mol. sieves / acetonitrile / 20 °C

11.1: methanol / 20 °C

With 2,6-dimethylpyridine; sodium hydroxide; sodium tetrahydroborate; tetrapropylammonium perruthennate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; B-iodo-9-BBN; triethylamine; 3-chloro-benzenecarboperoxoic acid; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; phosphate buffer; dichloromethane; N,N-dimethyl acetamide; acetonitrile; pentane; 1.1: Reduction / 2.1: Etherification / 3.1: Iodination / 3.2: Hydrolysis / 4.1: Substitution / 5.1: Hydrolysis / 6.1: Esterification / 7.1: Oxidation / 8.1: Cyclization / 9.1: Hydrolysis / 10.1: Oxidation / 11.1: Esterification;
DOI:10.1016/S0040-4039(00)00518-9

Reference yield:

: 289505-50-6
((2R,3S,4S,5S)-5-Benzyloxy-3-hydroxy-2-prop-2-ynyl-tetrahydro-pyran-4-yl)-methyl-carbamic acid tert-butyl ester

: 289505-54-0
(2S,3aR,6S,7R,7aR)-6-Benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-(tert-butoxycarbonyl-methyl-amino)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: (COCl)2; DMSO; i-Pr₂NEt / CH₂Cl₂ / -78 - 20 °C

2.1: NaBH₄ / tetrahydrofuran; methanol / -78 - 0 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

4.1: B-iodo-9-BBN / pentane / -20 °C

4.2: AcOH / pentane

5.1: PdCl₂(PPh₃)2 / tetrahydrofuran; N,N-dimethyl-acetamide / 35 °C

6.1: Bu₄NF / tetrahydrofuran / 20 °C

7.1: Et₃N / CH₂Cl₂ / 20 °C

8.1: 92 percent / m-chloroperbenzoic acid / CH₂Cl₂; aq. phosphate buffer / 20 °C / pH 7.0

9.1: camphorsulfonic acid / CH₂Cl₂ / 20 °C

10.1: 1N NaOH / tetrahydrofuran / 20 °C

11.1: tetrapropylammonium perrutenate; 4-methylmorpholine N-oxide; 4 Angstroem mol. sieves / acetonitrile / 20 °C

12.1: methanol / 20 °C

With 2,6-dimethylpyridine; sodium hydroxide; sodium tetrahydroborate; tetrapropylammonium perruthennate; oxalyl dichloride; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; B-iodo-9-BBN; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; phosphate buffer; dichloromethane; N,N-dimethyl acetamide; acetonitrile; pentane; 1.1: Oxidation / 2.1: Reduction / 3.1: Etherification / 4.1: Iodination / 4.2: Hydrolysis / 5.1: Substitution / 6.1: Hydrolysis / 7.1: Esterification / 8.1: Oxidation / 9.1: Cyclization / 10.1: Hydrolysis / 11.1: Oxidation / 12.1: Esterification;
DOI:10.1016/S0040-4039(00)00518-9

Reference yield:

: [5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-(2-iodo-allyl)-tetrahydro-pyran-4-yl]-methyl-carbamic acid tert-butyl ester

: 289505-54-0
(2S,3aR,6S,7R,7aR)-6-Benzyloxy-2-((S)-2-tert-butoxycarbonylamino-2-methoxycarbonyl-ethyl)-7-(tert-butoxycarbonyl-methyl-amino)-hexahydro-furo[3,2-b]pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: PdCl₂(PPh₃)2 / tetrahydrofuran; N,N-dimethyl-acetamide / 35 °C

2: Bu₄NF / tetrahydrofuran / 20 °C

3: Et₃N / CH₂Cl₂ / 20 °C

4: 92 percent / m-chloroperbenzoic acid / CH₂Cl₂; aq. phosphate buffer / 20 °C / pH 7.0

5: camphorsulfonic acid / CH₂Cl₂ / 20 °C

6: 1N NaOH / tetrahydrofuran / 20 °C

7: tetrapropylammonium perrutenate; 4-methylmorpholine N-oxide; 4 Angstroem mol. sieves / acetonitrile / 20 °C

8: methanol / 20 °C

With sodium hydroxide; tetrapropylammonium perruthennate; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; phosphate buffer; dichloromethane; N,N-dimethyl acetamide; acetonitrile; 1: Substitution / 2: Hydrolysis / 3: Esterification / 4: Oxidation / 5: Cyclization / 6: Hydrolysis / 7: Oxidation / 8: Esterification;
DOI:10.1016/S0040-4039(00)00518-9