(3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-ethyl-3aH,5H,6H,7H,7aH-pyrano[2,3-d][1,3]oxazole

Base Information

Chemical Name:(3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-ethyl-3aH,5H,6H,7H,7aH-pyrano[2,3-d][1,3]oxazole
CAS No.:1360560-48-0
Molecular Formula:C₃₀H₃₃NO₅
Molecular Weight:487.596
Hs Code.:

Synonyms:(3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-ethyl-3aH,5H,6H,7H,7aH-pyrano[2,3-d][1,3]oxazole

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Chemical Property of (3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-ethyl-3aH,5H,6H,7H,7aH-pyrano[2,3-d][1,3]oxazole

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Technology Process of (3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-ethyl-3aH,5H,6H,7H,7aH-pyrano[2,3-d][1,3]oxazole

There total 6 articles about (3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-ethyl-3aH,5H,6H,7H,7aH-pyrano[2,3-d][1,3]oxazole 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: 70.0%

: 107-12-0
propiononitrile

: 793672-55-6
p-methylphenyl 3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside

: 1360560-48-0
(3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-ethyl-3aH,5H,6H,7H,7aH-pyrano[2,3-d][1,3]oxazole

Guidance literature:: With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; Inert atmosphere; Molecular sieve; Cooling;
DOI:10.1002/chem.201100732

Reference yield:

: 3254-16-8,4435-05-6,19189-54-9,29748-21-8,50801-29-1,64727-26-0,64727-27-1,65338-02-5,67672-68-8,78418-55-0,80877-03-8,103002-27-3,103002-29-5,132562-62-0
3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose

: 1360560-48-0
(3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-ethyl-3aH,5H,6H,7H,7aH-pyrano[2,3-d][1,3]oxazole

Guidance literature:: Multi-step reaction with 4 steps

1.1: methanol; sodium / 20 °C

1.2: 0 °C / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / -15 - 20 °C / Inert atmosphere

3.1: methanol; sodium / dichloromethane / 20 °C

4.1: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / Inert atmosphere; Molecular sieve; Cooling

With methanol; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium; In dichloromethane;
DOI:10.1002/chem.201100732

Reference yield:

: 51532-75-3,16697-49-7,68681-00-5,68779-52-2,78418-56-1,125135-29-7,130694-47-2,130694-49-4,146864-77-9
3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose

: 1360560-48-0
(3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-ethyl-3aH,5H,6H,7H,7aH-pyrano[2,3-d][1,3]oxazole

Guidance literature:: Multi-step reaction with 3 steps

1: boron trifluoride diethyl etherate / dichloromethane / -15 - 20 °C / Inert atmosphere

2: methanol; sodium / dichloromethane / 20 °C

3: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / Inert atmosphere; Molecular sieve; Cooling

With methanol; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium; In dichloromethane;
DOI:10.1002/chem.201100732