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

Base Information

• Chemical Name: 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
• CAS No.: 106988-95-8
• Molecular Formula: C₃₁H₃₄O₅
• Molecular Weight: 486.608
• Mol file: 106988-95-8.mol

Synonyms: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

Chemical Property of 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

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-(hydroxymethyl)-1,7-O-isopropyliden-5-cyclohexen-1,2,3,4-tetrol

There total 9 articles about 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 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: 93.0%

1L-(1,2,4/3)-2,3,4-tri-O-benzyl-1-C-(hydroxymethyl)-5-cyclohexen-1,2,3,4-tetrol (106988-92-5) + 2,2-dimethoxy-propane (77-76-9) → 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:

toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 40 ℃;

DOI:10.1002/jlac.198719870350

Reference yield: 86.0%

2-Methoxypropene (116-11-0) + 1L-(1,2,4/3)-2,3,4-tri-O-benzyl-1-C-(hydroxymethyl)-5-cyclohexen-1,2,3,4-tetrol (106988-92-5) → 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:

With toluene-4-sulfonic acid; In dichloromethane; at 0 ℃; for 0.5h;

Reference yield:

(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-(hydroxymethyl)-1,7-O-isopropyliden-5-cyclohexen-1,2,3,4-tetrol (106988-95-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 15percent n-BuLi, 2.) H₂O / 1.) THF/hexane, -78 deg C, 1 h, 2.) THF/hexane, -78 deg C, 2 h

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

3: 93 percent / 4-toluenesulfonic acid / dimethylformamide / 40 °C

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

DOI:10.1002/jlac.198719870350

upstream raw materials:

2-Methoxypropene

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

2,2-dimethoxy-propane

benzyl bromide

Downstream raw materials:

(1'S,2'S,3'S,4'R,5'R,6'S)-3',4',5'-tribenzyloxy-2,2-dimethylspiro<1,3-dioxolane-4,2'-oxabicyclo<4.1.0>heptane>

<(1S,2S,4S,5S,6R)-5-benzyloxy-8,8,2',2'-tetramethylspiro<7,9-dioxabicyclo<4.3.0>nonane-2,4'-1',3'-dioxolan>-4-yl>-<(5''R,6''S,7''S,8''S,9''R,10''S)-8'',9'',10''-tribenzyloxy-6''-hydroxy-2'',2''-dimethyl-1'',3''-dioxaspiro<4.5>decan-7''-yl>amine

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

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