Allyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethyl)-amine

Base Information

Chemical Name:Allyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethyl)-amine
CAS No.:205192-09-2
Molecular Formula:C₃₁H₃₇NO₄S
Molecular Weight:519.705
Hs Code.:

Synonyms:Allyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethyl)-amine

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Chemical Property of Allyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethyl)-amine

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Technology Process of Allyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethyl)-amine

There total 4 articles about Allyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethyl)-amine 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:

: 89157-97-1
1,6-anhydro-2,3,4-tri-O-benzyl-β-L-idopyranose

: 205192-09-2
Allyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethyl)-amine

Guidance literature:: Multi-step reaction with 3 steps

1: 88.5 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 40 h

2: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) CH₂Cl₂, from -78 deg C to RT

3: NaCNBH₃ / methanol / 0.25 h

With oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane;
DOI:10.1021/ja972599h

Reference yield:

: 205192-07-0
((2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-methanol

: 205192-09-2
Allyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethyl)-amine

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) CH₂Cl₂, from -78 deg C to RT

2: NaCNBH₃ / methanol / 0.25 h

With oxalyl dichloride; sodium cyanoborohydride; dimethyl sulfoxide; triethylamine; In methanol;
DOI:10.1021/ja972599h

Reference yield:

: 641635-63-4
((3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methanol

: 205192-09-2
Allyl-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-ylmethyl)-amine

Guidance literature:: Multi-step reaction with 4 steps

1: 80 percent / AcOH, aq. HCl / 1 h / 70 °C

2: 88.5 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 40 h

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) CH₂Cl₂, from -78 deg C to RT

4: NaCNBH₃ / methanol / 0.25 h

With hydrogenchloride; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane;
DOI:10.1021/ja972599h