(1S,2R,3S,5S)-2,3-Bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane

Base Information

• Chemical Name: (1S,2R,3S,5S)-2,3-Bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane
• CAS No.: 616895-53-5
• Molecular Formula: C₂₀H₂₂O₄
• Molecular Weight: 326.392
• Mol file: 616895-53-5.mol

Synonyms:

Chemical Property of (1S,2R,3S,5S)-2,3-Bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3S,5S)-2,3-Bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane

There total 6 articles about (1S,2R,3S,5S)-2,3-Bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane 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:

(S)-1-(α-furyl)-1,2-ethanediol (61243-05-8) → (1S,2R,3S,5S)-2,3-Bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane (616895-53-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: O₂; TPP / methanol; CH₂Cl₂

1.2: 93 percent / Me₂S

2.1: 66 percent / TsOH; MgSO₄ / acetonitrile

3.1: H₂ / Pd/C / ethyl acetate

3.2: NaHMDS / tetrahydrofuran / -78 °C

3.3: 84 percent / tetrahydrofuran

4.1: 60 percent / Bu₃SnH; LiCl / (Ph₃P)4Pd / diethyl ether

5.1: MCPBA; NaHCO₃ / CH₂Cl₂

5.2: KOH / H₂O

6.1: NaH / dimethylsulfoxide; tetrahydrofuran

With hydrogen; oxygen; tri-n-butyl-tin hydride; thiamine diphosphate; sodium hydride; sodium hydrogencarbonate; magnesium sulfate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium chloride; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4020(03)00370-3

Reference yield:

(-)-(1S,5S)-Isolevoglucosenone (33647-85-7) → (1S,2R,3S,5S)-2,3-Bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane (616895-53-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: H₂ / Pd/C / ethyl acetate

1.2: NaHMDS / tetrahydrofuran / -78 °C

1.3: 84 percent / tetrahydrofuran

2.1: 60 percent / Bu₃SnH; LiCl / (Ph₃P)4Pd / diethyl ether

3.1: MCPBA; NaHCO₃ / CH₂Cl₂

3.2: KOH / H₂O

4.1: NaH / dimethylsulfoxide; tetrahydrofuran

With hydrogen; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; lithium chloride; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate;

DOI:10.1016/S0040-4020(03)00370-3

Reference yield:

6-hydroxy-2-hydroxymethyl-6H-pyran-3-one (617711-44-1) → (1S,2R,3S,5S)-2,3-Bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane (616895-53-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 66 percent / TsOH; MgSO₄ / acetonitrile

2.1: H₂ / Pd/C / ethyl acetate

2.2: NaHMDS / tetrahydrofuran / -78 °C

2.3: 84 percent / tetrahydrofuran

3.1: 60 percent / Bu₃SnH; LiCl / (Ph₃P)4Pd / diethyl ether

4.1: MCPBA; NaHCO₃ / CH₂Cl₂

4.2: KOH / H₂O

5.1: NaH / dimethylsulfoxide; tetrahydrofuran

With hydrogen; tri-n-butyl-tin hydride; sodium hydride; sodium hydrogencarbonate; magnesium sulfate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium chloride; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate; acetonitrile;

DOI:10.1016/S0040-4020(03)00370-3

upstream raw materials:

benzyl chloride

(S)-1-(α-furyl)-1,2-ethanediol

(-)-(1S,5S)-Isolevoglucosenone

(1R,5S)-6,8-Dioxa-bicyclo[3.2.1]oct-2-ene

Downstream raw materials:

((2S,3R,4S,6S)-6-Allyl-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-methanol

((2S,3R,4S,6R)-6-Allyl-3,4-bis-benzyloxy-tetrahydro-pyran-2-yl)-methanol

[2,3-di-O-benzyl-4,6-dideoxy-6-(methoxycarbonyl)-D-gluco-β-C-pyranosyl]aldehyde

{(2S,4S,5R,6S)-4,5-Bis-benzyloxy-6-[(E)-2-((1S,2S,3S)-2-hydroxymethyl-3-methyl-cyclopropyl)-vinyl]-tetrahydro-pyran-2-yl}-acetic acid methyl ester