(3R,4aS,6R,7S,8R,8aR)-7,8-bis-benzyloxy-6-benzyloxymethyl-3-methyl-hexahydro-pyrano[2,3-b][1,4]oxazin-2-one

Base Information

Chemical Name:(3R,4aS,6R,7S,8R,8aR)-7,8-bis-benzyloxy-6-benzyloxymethyl-3-methyl-hexahydro-pyrano[2,3-b][1,4]oxazin-2-one
CAS No.:671792-69-1
Molecular Formula:C₃₀H₃₃NO₆
Molecular Weight:503.595
Hs Code.:

Synonyms:(3R,4aS,6R,7S,8R,8aR)-7,8-bis-benzyloxy-6-benzyloxymethyl-3-methyl-hexahydro-pyrano[2,3-b][1,4]oxazin-2-one

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Chemical Property of (3R,4aS,6R,7S,8R,8aR)-7,8-bis-benzyloxy-6-benzyloxymethyl-3-methyl-hexahydro-pyrano[2,3-b][1,4]oxazin-2-one

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Technology Process of (3R,4aS,6R,7S,8R,8aR)-7,8-bis-benzyloxy-6-benzyloxymethyl-3-methyl-hexahydro-pyrano[2,3-b][1,4]oxazin-2-one

There total 4 articles about (3R,4aS,6R,7S,8R,8aR)-7,8-bis-benzyloxy-6-benzyloxymethyl-3-methyl-hexahydro-pyrano[2,3-b][1,4]oxazin-2-one 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: 77.0%

: 671792-67-9
O-(2-amino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-D-lactic acid

: 671792-69-1
(3R,4aS,6R,7S,8R,8aR)-7,8-bis-benzyloxy-6-benzyloxymethyl-3-methyl-hexahydro-pyrano[2,3-b][1,4]oxazin-2-one

Guidance literature:: With diphenylphosphoranyl azide; triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 1.5h;
DOI:10.1055/s-2003-42494

Reference yield:

: 117136-22-8
3,4,6-tri-O-benzyl-1,2-dideoxy-2-nitro-D-arabino-hex-1-enopyranose

: 671792-69-1
(3R,4aS,6R,7S,8R,8aR)-7,8-bis-benzyloxy-6-benzyloxymethyl-3-methyl-hexahydro-pyrano[2,3-b][1,4]oxazin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 38 percent / 3 Angstroem molecular sieves; t-BuOK / toluene / 12 h / 20 °C

2: 94 percent / H₂ / Raney Ni (T₄) / ethanol / 48 h / 20 °C / atmospheric pressure

3: 96 percent / TFA / CH₂Cl₂ / 12 h / 20 °C

4: 77 percent / Et₃N; diphenylphosphoryl azide / dimethylformamide / 1.5 h / 20 °C

With 3 A molecular sieve; diphenylphosphoranyl azide; potassium tert-butylate; hydrogen; triethylamine; trifluoroacetic acid; Raney Ni (T₄); In ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Michael addition;
DOI:10.1055/s-2003-42494

Reference yield:

: 671792-64-6
tert-butyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-D-lactate

: 671792-69-1
(3R,4aS,6R,7S,8R,8aR)-7,8-bis-benzyloxy-6-benzyloxymethyl-3-methyl-hexahydro-pyrano[2,3-b][1,4]oxazin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / H₂ / Raney Ni (T₄) / ethanol / 48 h / 20 °C / atmospheric pressure

2: 96 percent / TFA / CH₂Cl₂ / 12 h / 20 °C

3: 77 percent / Et₃N; diphenylphosphoryl azide / dimethylformamide / 1.5 h / 20 °C

With diphenylphosphoranyl azide; hydrogen; triethylamine; trifluoroacetic acid; Raney Ni (T₄); In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2003-42494