(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>

Base Information

• Chemical Name: (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>
• CAS No.: 106988-97-0
• Molecular Formula: C₃₁H₃₄O₆
• Molecular Weight: 502.607
• Mol file: 106988-97-0.mol

Synonyms:(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>

Chemical Property of (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>

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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>

There total 9 articles about (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> 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: 67.0%

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) → (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> (106988-97-0)

Guidance literature:

With phosphate buffer pH 8; 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; at 60 ℃; for 45h;

Reference yield:

1L-(1,2,4/3)-2,3,4-tri-O-benzyl-1-C-(hydroxymethyl)-5-cyclohexen-1,2,3,4-tetrol (106988-92-5) → (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> (106988-97-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / PTSA / CH₂Cl₂ / 0.5 h / 0 °C

2: 67 percent / MCPBA, aq. phosphate buffer pH 8 / 1,2-dichloro-ethane / 45 h / 60 °C

With phosphate buffer pH 8; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1,2-dichloro-ethane;

Reference yield:

(4S,5R,6S)-4,5,6-tris-benzyloxycyclohex-2-en-1-one (85798-11-4) → (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> (106988-97-0)

Guidance literature:

Multi-step reaction with 4 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

4: 36 percent / NaHCO₃, 80percent 3-chloroperoxybenzoic acid / CH₂Cl₂ / 528 h / Ambient temperature

With sodium tetrahydroborate; n-butyllithium; water; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; mercury dichloride; mercury(II) oxide; toluene-4-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/jlac.198719870350

upstream raw materials:

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

benzyl bromide

(1R)-(-)-1,2,3-tri-O-acetyl-(1,3/2,4,6)-4-bromo-6-bromomethyl-1,2,3-cyclohexanetriol

1D-(1,3/2)-1,2,3-tri-O-benzyl-4-methylene-5-cyclohexen-1,2,3-triol

Downstream raw materials:

<(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-azido-1,5,6-tri-O-benzyl-2-desoxy-4-C-(hydroxymethyl)-4,7-O-isopropyliden-muco-inosit

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

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