1,4-anhydro-3-[(6R)-5-{[(benzyloxy)carbonyl]amino}-5-deoxy-1,2-O-isopropylidene-β-D-idofuranos-6C-yl]-3-deoxy-2,6-bis-O-(methoxymethyl)-α-D-galactopyranose

Base Information

Chemical Name:1,4-anhydro-3-[(6R)-5-{[(benzyloxy)carbonyl]amino}-5-deoxy-1,2-O-isopropylidene-β-D-idofuranos-6C-yl]-3-deoxy-2,6-bis-O-(methoxymethyl)-α-D-galactopyranose
CAS No.:263405-71-6
Molecular Formula:C₂₇H₃₉NO₁₃
Molecular Weight:585.606
Hs Code.:

1,4-anhydro-3-[(6R)-5-{[(benzyloxy)carbonyl]amino}-5-deoxy-1,2-O-isopropylidene-β-D-idofuranos-6C-yl]-3-deoxy-2,6-bis-O-(methoxymethyl)-α-D-galactopyranose

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Chemical Property of 1,4-anhydro-3-[(6R)-5-{[(benzyloxy)carbonyl]amino}-5-deoxy-1,2-O-isopropylidene-β-D-idofuranos-6C-yl]-3-deoxy-2,6-bis-O-(methoxymethyl)-α-D-galactopyranose

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Technology Process of 1,4-anhydro-3-[(6R)-5-{[(benzyloxy)carbonyl]amino}-5-deoxy-1,2-O-isopropylidene-β-D-idofuranos-6C-yl]-3-deoxy-2,6-bis-O-(methoxymethyl)-α-D-galactopyranose

There total 7 articles about 1,4-anhydro-3-[(6R)-5-{[(benzyloxy)carbonyl]amino}-5-deoxy-1,2-O-isopropylidene-β-D-idofuranos-6C-yl]-3-deoxy-2,6-bis-O-(methoxymethyl)-α-D-galactopyranose 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:

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

: 263405-70-5
3-[(6R)-5-amino-5-deoxy-1,2-O-isopropylidene-β-D-idofuranos-6C-yl]-1,4-anhydro-3-deoxy-2,6-bis-O-(methoxymethyl)-α-D-galactopyranose

: 263405-71-6
1,4-anhydro-3-[(6R)-5-{[(benzyloxy)carbonyl]amino}-5-deoxy-1,2-O-isopropylidene-β-D-idofuranos-6C-yl]-3-deoxy-2,6-bis-O-(methoxymethyl)-α-D-galactopyranose

Guidance literature:: With sodium hydrogencarbonate; In ethanol; at 25 ℃; for 1.5h;
DOI:10.1002/(SICI)1522-2675(20000119)83:1<193::AID-HLCA193>3.0.CO;2-I

Reference yield:

: 223138-07-6
(-)-(3aS,5S,6S,6aR)-3a,5,6,6a-tetrahydro-5,6-isopropylidenedioxyfuro<2,3-d>isoxazole-3-carbaldehyde

: 263405-71-6
1,4-anhydro-3-[(6R)-5-{[(benzyloxy)carbonyl]amino}-5-deoxy-1,2-O-isopropylidene-β-D-idofuranos-6C-yl]-3-deoxy-2,6-bis-O-(methoxymethyl)-α-D-galactopyranose

Guidance literature:: Multi-step reaction with 7 steps

1.1: BuLi; Me₃SiNHSiMe₃ / tetrahydrofuran; hexane / 3 h / -78 °C

1.2: 2,6-lutidine / CH₂Cl₂ / 6 h / 0 - 25 °C

1.3: 41 percent / NaBH₄ / methanol / 0 °C

2.1: 97 percent / EtN(i-Pr)2 / CH₂Cl₂ / 21 h / 0 - 25 °C

3.1: 86 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 16 h / -78 - 25 °C

4.1: OsO₄; NaHCO₃; Me₃NO*2H₂O / CCl₄; tetrahydrofuran; H₂O / 2 h / 25 °C

5.1: (i-Pr)2NEt / CH₂Cl₂ / 16 h / 0 - 25 °C

6.1: LiAlH / diethyl ether / 120 h / 25 °C

7.1: NaHCO₃ / aq. ethanol / 1.5 h / 25 °C

With osmium(VIII) oxide; n-butyllithium; trimethylamine-N-oxide; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; hexane; dichloromethane; water; 1.1: Addition / 1.2: silylation / 1.3: Reduction / 2.1: Substitution / 3.1: Elimination / 4.1: double hydroxylation / 5.1: Substitution / 6.1: Reduction / 7.1: Substitution;
DOI:10.1002/(SICI)1522-2675(20000119)83:1<193::AID-HLCA193>3.0.CO;2-I

Reference yield:

: 263405-47-6
(-)-(1S,2R,3S,4R)-3-exo-{(S)-[(tert-butyl)dimethylsilyloxy][(3aS,4aS,7aR,7bR)-3a,4a,7a,7b-tetrahydro-6,6-dimethyl[1,3]dioxolo[4,5]furo[2,3-d]isoxazol-3-yl]methyl}-6-chloro-2-endo-(methoxymethoxy)-7-oxabicyclo[2.2.1]hept-5-ene

: 263405-71-6
1,4-anhydro-3-[(6R)-5-{[(benzyloxy)carbonyl]amino}-5-deoxy-1,2-O-isopropylidene-β-D-idofuranos-6C-yl]-3-deoxy-2,6-bis-O-(methoxymethyl)-α-D-galactopyranose

Guidance literature:: Multi-step reaction with 4 steps

1: OsO₄; NaHCO₃; Me₃NO*2H₂O / CCl₄; tetrahydrofuran; H₂O / 2 h / 25 °C

2: (i-Pr)2NEt / CH₂Cl₂ / 16 h / 0 - 25 °C

3: LiAlH / diethyl ether / 120 h / 25 °C

4: NaHCO₃ / aq. ethanol / 1.5 h / 25 °C

With osmium(VIII) oxide; trimethylamine-N-oxide; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; 1: double hydroxylation / 2: Substitution / 3: Reduction / 4: Substitution;
DOI:10.1002/(SICI)1522-2675(20000119)83:1<193::AID-HLCA193>3.0.CO;2-I