methyl (3aR,4R,6S,7aS)-3-acetyl-4-((4S,5R)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(dibutoxyphosphoryloxy)-2-oxohexahydro-2H-pyrano[3,4-d]oxazole-6-carboxylate

Base Information

Chemical Name:methyl (3aR,4R,6S,7aS)-3-acetyl-4-((4S,5R)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(dibutoxyphosphoryloxy)-2-oxohexahydro-2H-pyrano[3,4-d]oxazole-6-carboxylate
CAS No.:1447701-12-3
Molecular Formula:C₃₁H₄₆NO₁₃P
Molecular Weight:671.679
Hs Code.:

methyl (3aR,4R,6S,7aS)-3-acetyl-4-((4S,5R)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(dibutoxyphosphoryloxy)-2-oxohexahydro-2H-pyrano[3,4-d]oxazole-6-carboxylate

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Chemical Property of methyl (3aR,4R,6S,7aS)-3-acetyl-4-((4S,5R)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(dibutoxyphosphoryloxy)-2-oxohexahydro-2H-pyrano[3,4-d]oxazole-6-carboxylate

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Technology Process of methyl (3aR,4R,6S,7aS)-3-acetyl-4-((4S,5R)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(dibutoxyphosphoryloxy)-2-oxohexahydro-2H-pyrano[3,4-d]oxazole-6-carboxylate

There total 2 articles about methyl (3aR,4R,6S,7aS)-3-acetyl-4-((4S,5R)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(dibutoxyphosphoryloxy)-2-oxohexahydro-2H-pyrano[3,4-d]oxazole-6-carboxylate 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: 32.0%

: 1447701-10-1
methyl (3aR,4R,6S,7aS)-3-acetyl-4-((4S,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-2-oxo-6-(phenylsulfanyl)hexahydro-2H-pyrano[3,4-d]oxazole-6-carboxylate

: 107-66-4
dibutyl phosphate

: 1447701-12-3
methyl (3aR,4R,6S,7aS)-3-acetyl-4-((4S,5R)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(dibutoxyphosphoryloxy)-2-oxohexahydro-2H-pyrano[3,4-d]oxazole-6-carboxylate

Guidance literature:: methyl (3aR,4R,6S,7aS)-3-acetyl-4-((4S,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl)-2-oxo-6-(phenylsulfanyl)hexahydro-2H-pyrano[3,4-d]oxazole-6-carboxylate; dibutyl phosphate; In dichloromethane; at 25 ℃; for 3h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; trifluorormethanesulfonic acid; In diethyl ether; at 0 ℃; for 10h; Molecular sieve; Inert atmosphere;
DOI:10.1021/ja403609x

Reference yield:

: C₂₇H₃₁NO₈S

: 1447701-12-3
methyl (3aR,4R,6S,7aS)-3-acetyl-4-((4S,5R)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(dibutoxyphosphoryloxy)-2-oxohexahydro-2H-pyrano[3,4-d]oxazole-6-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C

2.1: dichloromethane / 3 h / 25 °C / Molecular sieve; Inert atmosphere

2.2: 10 h / 0 °C / Molecular sieve; Inert atmosphere

With N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/ja403609x

Reference yield:

: 1447700-84-6
(2S,3R,4S,5R,6R)-6-((benzyloxy)methyl)-4,5-dihydroxy-2-(p-tolylthio)tetrahydro-2H-pyran-3-yl benzoate

: 1447701-12-3
methyl (3aR,4R,6S,7aS)-3-acetyl-4-((4S,5R)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(dibutoxyphosphoryloxy)-2-oxohexahydro-2H-pyrano[3,4-d]oxazole-6-carboxylate

: 1447701-16-7
methyl (3aR,4R,6S,7aS)-3-acetyl-6-((2S,3R,4S,5S,6R)-3-(benzoyloxy)-6-(benzyloxymethyl)-5-hydroxy-2-(p-tolylthio)tetrahydro-2H-pyran-4-yloxy)-4-((4S,5R)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazole-6-carboxylate

: methyl (3aR,4R,6R,7aS)-3-acetyl-6-((2S,3R,4S,5S,6R)-3-(benzoyloxy)-6-(benzyloxymethyl)-5-hydroxy-2-(p-tolylthio)tetrahydro-2H-pyran-4-yloxy)-4-((4S,5R)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-oxohexahydro-2H-pyrano[3,4-d]oxazole-6-carboxylate

Guidance literature:: (2S,3R,4S,5R,6R)-6-((benzyloxy)methyl)-4,5-dihydroxy-2-(p-tolylthio)tetrahydro-2H-pyran-3-yl benzoate; methyl (3aR,4R,6S,7aS)-3-acetyl-4-((4S,5R)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-(dibutoxyphosphoryloxy)-2-oxohexahydro-2H-pyrano[3,4-d]oxazole-6-carboxylate; In dichloromethane; at 25 ℃; for 2h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 2h; Overall yield = 80 %; Overall yield = 0.51 g; Molecular sieve; Inert atmosphere;
DOI:10.1021/ja403609x