(2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-6-propa-1,2-dienyl-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-6-propa-1,2-dienyl-tetrahydro-pyran-3-ol
• CAS No.: 106929-17-3
• Molecular Formula: C₄₃H₄₆O₈
• Molecular Weight: 690.833
• Mol file: 106929-17-3.mol

Synonyms:

Chemical Property of (2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-6-propa-1,2-dienyl-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-6-propa-1,2-dienyl-tetrahydro-pyran-3-ol

There total 1 articles about (2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-6-propa-1,2-dienyl-tetrahydro-pyran-3-ol 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: 70.0%

trimethyl(propargyl)silane (13361-64-3) + 4-Nitro-benzoic acid (2R,3S,4R,5R,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl ester (106974-28-1) → (2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-6-propa-1,2-dienyl-tetrahydro-pyran-3-ol (106929-17-3)

Guidance literature:

In acetonitrile;

DOI:10.1021/jo00383a045

Reference yield:

(2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-6-propa-1,2-dienyl-tetrahydro-pyran-3-ol (106929-17-3) → Benzoic acid (2R,3R,4R,5R,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-hydroxy-tetrahydro-pyran-2-ylmethyl ester (106929-14-0,106974-27-0,106974-30-5,138181-85-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, 2.) NaBH₄ / 1.) CH₃OH, -78 deg C, 2.) ethanol, 0 deg C

2: pyridinium / CH₂Cl₂ / Ambient temperature

With pyridine; sodium tetrahydroborate; ozone; In dichloromethane;

DOI:10.1021/jo00383a045

Reference yield:

(2R,3R,4R,5R)-4,5-Bis-benzyloxy-2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-6-propa-1,2-dienyl-tetrahydro-pyran-3-ol (106929-17-3) → Benzoic acid (2R,3R,4S,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-oxo-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) O₃, 2.) NaBH₄ / 1.) CH₃OH, -78 deg C, 2.) ethanol, 0 deg C

2: pyridinium / CH₂Cl₂ / Ambient temperature

3: (COCl)2, DMSO

With pyridine; sodium tetrahydroborate; oxalyl dichloride; ozone; dimethyl sulfoxide; In dichloromethane;

DOI:10.1021/jo00383a045

upstream raw materials:

trimethyl(propargyl)silane

4-Nitro-benzoic acid (2R,3S,4R,5R,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl ester

Downstream raw materials:

(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-2-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-6-hydroxymethyl-tetrahydro-pyran-3-ol

Benzoic acid (2R,3R,4R,5R,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-hydroxy-tetrahydro-pyran-2-ylmethyl ester

Benzoic acid (2R,3R,4R,6R)-3,4-bis-benzyloxy-6-((1S,2R,3S,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-ylmethyl)-5-hydroxy-tetrahydro-pyran-2-ylmethyl ester