1L-(1,2,4/3)-2,3,4-tri-O-benzyl-1-C-(5-methyl-1,3,5-dithiazinan-2-yl)-5-cyclohexen-1,2,3,4-tetrol

Base Information

• Chemical Name: 1L-(1,2,4/3)-2,3,4-tri-O-benzyl-1-C-(5-methyl-1,3,5-dithiazinan-2-yl)-5-cyclohexen-1,2,3,4-tetrol
• CAS No.: 106988-91-4
• Molecular Formula: C₃₁H₃₅NO₄S₂
• Molecular Weight: 549.755
• Mol file: 106988-91-4.mol

Synonyms:

Chemical Property of 1L-(1,2,4/3)-2,3,4-tri-O-benzyl-1-C-(5-methyl-1,3,5-dithiazinan-2-yl)-5-cyclohexen-1,2,3,4-tetrol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1L-(1,2,4/3)-2,3,4-tri-O-benzyl-1-C-(5-methyl-1,3,5-dithiazinan-2-yl)-5-cyclohexen-1,2,3,4-tetrol

There total 1 articles about 1L-(1,2,4/3)-2,3,4-tri-O-benzyl-1-C-(5-methyl-1,3,5-dithiazinan-2-yl)-5-cyclohexen-1,2,3,4-tetrol 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:

5-methyl-[1,3,5]dithiazinane (6302-94-9) + (4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one (85798-11-4) → 1L-(1,2,4/3)-2,3,4-tri-O-benzyl-1-C-(5-methyl-1,3,5-dithiazinan-2-yl)-5-cyclohexen-1,2,3,4-tetrol (106988-91-4) + 1D-(2,4/1,3)-1,2,3-tri-O-benzyl-4-C-(5-methyl-1,3,5-dithiazinan-2-yl)-5-cyclohexen-1,2,3,4-tetrol (107079-33-4)

Guidance literature:

With n-butyllithium; water; Yield given. Multistep reaction; 1.) THF/hexane, -78 deg C, 1 h, 2.) THF/hexane, -78 deg C, 2 h;

DOI:10.1002/jlac.198719870350

Reference yield:

1L-(1,2,4/3)-2,3,4-tri-O-benzyl-1-C-(5-methyl-1,3,5-dithiazinan-2-yl)-5-cyclohexen-1,2,3,4-tetrol (106988-91-4) → 1L-2-amino-2-desoxy-4-C-(hydroxymethyl)-muco-inosit-hydrochlorid (106989-03-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) HgO/HgCl₂, 2.) NaBH₄ / 1) CH₃CN/H₂O

2: 90 percent / NaHCO₃, 80percent 3-chloroperoxybenzoic acid / CH₂Cl₂ / 144 h / Ambient temperature

3: 60 percent / NaH / dimethylformamide / 0 °C

4: 71 percent / NaN₃ / dimethylformamide / 96 h / 130 °C

5: 90 percent / H₂, 3 N HCl / 10 percent Pd/C / methanol / 30 h

With hydrogenchloride; sodium tetrahydroborate; sodium azide; hydrogen; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; mercury dichloride; mercury(II) oxide; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/jlac.198719870350

Reference yield:

1L-(1,2,4/3)-2,3,4-tri-O-benzyl-1-C-(5-methyl-1,3,5-dithiazinan-2-yl)-5-cyclohexen-1,2,3,4-tetrol (106988-91-4) → 1L-(1,2,4/3)-2,3,4-tri-O-benzyl-1-C-(hydroxymethyl)-1,7-O-isopropyliden-5-cyclohexen-1,2,3,4-tetrol (106988-95-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) HgO/HgCl₂, 2.) NaBH₄ / 1) CH₃CN/H₂O

2: 93 percent / 4-toluenesulfonic acid / dimethylformamide / 40 °C

With sodium tetrahydroborate; mercury dichloride; mercury(II) oxide; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1002/jlac.198719870350

upstream raw materials:

5-methyl-[1,3,5]dithiazinane

(4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one

Downstream raw materials:

1L-(1,2,4/3)-2,3,4-tri-O-benzyl-1-C-(hydroxymethyl)-5-cyclohexen-1,2,3,4-tetrol

1L-1,2-anhydro-3,4,5,6-tetra-O-benzyl-6-C-(benzyloxymethyl)-chiro-inosit

1L-2-azido-1,4,5,6-tetra-O-benzyl-2-desoxy-4-C-(benzyloxymethyl)-muco-inosit

1L-2-amino-2-desoxy-4-C-(hydroxymethyl)-muco-inosit-hydrochlorid

Refernces