Sulfamic acid (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-sulfamoyloxy-cyclohexyl ester

Base Information

• Chemical Name: Sulfamic acid (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-sulfamoyloxy-cyclohexyl ester
• CAS No.: 145508-52-7
• Molecular Formula: C₂₇H₃₃N₃O₁₂S₃
• Molecular Weight: 687.77
• Mol file: 145508-52-7.mol

Synonyms:Sulfamic acid (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-sulfamoyloxy-cyclohexyl ester

Chemical Property of Sulfamic acid (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-sulfamoyloxy-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Sulfamic acid (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-sulfamoyloxy-cyclohexyl ester

There total 5 articles about Sulfamic acid (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-sulfamoyloxy-cyclohexyl ester 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:

(±)-2,3,6-tri-O-benzyl-myo-inositol (98906-30-0,104873-76-9,111466-07-0,114297-88-0,114297-91-5,114419-08-8,115184-71-9,115509-75-6,115509-76-7,118354-54-4,118354-55-5,128163-34-8,129706-80-5,136521-84-1,149713-88-2,149713-95-1) → Sulfamic acid (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-sulfamoyloxy-cyclohexyl ester (145508-52-7)

Guidance literature:

With sulphamoyl chloride; sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 2h;

DOI:10.1016/S0040-4039(00)97207-1

Reference yield:

1-O-Allyl-2,3,6-tri-O-benzyl-4,5-O-isopropylidene-myo-inositol (114218-19-8,114297-81-3) → Sulfamic acid (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-sulfamoyloxy-cyclohexyl ester (145508-52-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / (1,5-cyclo-octadiene)-bis-(methyldiphenylphosphine)iridium hexafluorophosphate, H₂ / tetrahydrofuran / 4 h

2: 96 percent / 1M HCl / acetone / 0.17 h / Heating

3: 1) NaH, 2) sulfamoyl chloride / 1) DMF, 0 deg C, 5 min, 2) 0 deg C, 2 h

With hydrogenchloride; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; sulphamoyl chloride; hydrogen; sodium hydride; In tetrahydrofuran; acetone;

DOI:10.1016/0008-6215(92)85044-Z

Reference yield:

(+/-)-1-O-allyl-3,6-di-O-benzyl-4,5-O-isopropylidene-myo-inositol (114218-23-4,114297-87-9,114298-50-9) → Sulfamic acid (1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-sulfamoyloxy-cyclohexyl ester (145508-52-7)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH / dimethylformamide

2: 100 percent / cyclooctadiene-bis(methyldiphenylphosphine)-iridium hexafluorophosphate

3: 96 percent / 0.1N HCl / dioxane; methanol

4: NH₂SO₂Cl, NaH / dimethylformamide / 2 h / 0 °C

With hydrogenchloride; sulphamoyl chloride; sodium hydride; cyclooctadiene-bis(methyldiphenylphosphine)-iridium hexafluorophosphate; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97207-1

upstream raw materials:

(±)-2,3,6-tri-O-benzyl-myo-inositol

1-O-Allyl-2,3,6-tri-O-benzyl-4,5-O-isopropylidene-myo-inositol

2,3,6-tri-O-benzyl-4,5-isopropylidene-1-O-(prop-1-enyl)-myo-inositol

(+/-)-1-O-allyl-3,6-di-O-benzyl-4,5-O-isopropylidene-myo-inositol

Downstream raw materials:

myo-Inositol 1,4,5-trissulphonamide