(3S,4R,5S,6S)-2-Methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (3S,4R,5S,6S)-2-Methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 65310-00-1
• Molecular Formula: C7H14 O5
• Molecular Weight: 178.185
• Hs Code.: 29400000
• DSSTox Substance ID: DTXSID901296166
• Nikkaji Number: J1.470.446I
• Mol file: 65310-00-1.mol

Synonyms:65310-00-1;(3S,4R,5S,6S)-2-Methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol;METHYL-L-FUCOPYRANOSIDE;methyl l-fucopyranoside;(3S,4R,5S,6S)-2-methoxy-6-methyloxane-3,4,5-triol;methyl 6-deoxy-l-galactopyranoside;Methyl Fucopyranoside;SCHEMBL2502348;DTXSID901296166;AKOS027320307;L-GALACTOPYRANOSIDE,METHYL 6-DEOXY-;W-203415

Chemical Property of (3S,4R,5S,6S)-2-Methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

• Melting Point: 150-152°C
• Refractive Index: 1.4330 (estimate)
• Boiling Point: 230.4°C (rough estimate)
• PKA: 13.05±0.70(Predicted)
• PSA: 79.15000
• Density: 1.1571 (rough estimate)
• LogP: -1.53970
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly), Water (Slightly)
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 178.08412354
• Heavy Atom Count: 12
• Complexity: 151

Purity/Quality:

98%min ^*data from raw suppliers

Methyl L-fucopyranoside ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC)O)O)O
• Isomeric SMILES: C[C@H]1[C@H]([C@H]([C@@H](C(O1)OC)O)O)O
• Uses: Methyl Fucopyranoside (α,β mixture) (cas# 65310-00-1) is a compound useful in organic synthesis.

Technology Process of (3S,4R,5S,6S)-2-Methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol

There total 106 articles about (3S,4R,5S,6S)-2-Methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol 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: 98.0%

Methyl 2,3,4-tri-O-acetyl-6-deoxy-β-L-galactopyranoside (24332-97-6) → methyl β-L-fucopyranoside (1128-40-1,1198-82-9,2592-55-4,5155-43-1,6340-52-9,10503-91-0,14009-07-5,14687-15-1,14917-55-6,15814-59-2,24332-98-7,34299-65-5,42214-00-6,42214-11-9,57783-34-3,57783-36-5,57783-38-7,57783-40-1,57783-42-3,58525-46-5,58525-47-6,58525-48-7,62182-01-8,62182-02-9,63864-94-8,65310-00-1,65941-62-0,68069-80-7,71116-57-9,72274-54-5,72274-55-6,73036-22-3,83198-64-5,85505-15-3,102517-74-8,109718-80-1,109718-81-2,125280-09-3,129172-95-8)

Guidance literature:

With sodium methylate; In methanol; for 1h; Ambient temperature;

Reference yield: 98.0%

methanol (67-56-1) + L-rhamnose (73-34-7) → methyl L-rhamnopyranoside (1128-40-1,1198-82-9,2592-55-4,5155-43-1,6340-52-9,10503-91-0,14009-07-5,14687-15-1,14917-55-6,15814-59-2,24332-98-7,34299-65-5,42214-00-6,42214-11-9,57783-34-3,57783-36-5,57783-38-7,57783-40-1,57783-42-3,58525-46-5,58525-47-6,58525-48-7,62182-01-8,62182-02-9,65310-00-1,65941-62-0,68069-80-7,71116-57-9,72274-54-5,72274-55-6,73036-22-3,83198-64-5,85505-15-3,102517-74-8,109718-80-1,109718-81-2,125280-09-3,129172-95-8,63864-94-8)

Guidance literature:

With Amberlist IR-120(H⁺); for 48h; Heating;

DOI:10.1021/jo010522c

Reference yield: 45.0%

9-(2',3'-O-benzylidene-5'-O-[(2'',3'',4''-tri-O-benzyl-α,β-L-fucopyranosyl)oxycarbonylaminosulfonyl]-β-D-ribofuranosyl)-2-N-(phenylacetyl)-guanine → 9-(5'-O-[(α-L-fucopyranosyl)oxycarbonylaminosulfonyl]-β-D-ribofuranosyl)-2-N-(phenylacetyl)-guanine + 9-(5'-O-[(β-L-fucopyranosyl)oxycarbonylaminosulfonyl]-β-D-ribofuranosyl)-2-N-(phenylacetyl)-guanine + methyl β-L-fucopyranoside (1128-40-1,1198-82-9,2592-55-4,5155-43-1,6340-52-9,10503-91-0,14009-07-5,14687-15-1,14917-55-6,15814-59-2,24332-98-7,34299-65-5,42214-00-6,42214-11-9,57783-34-3,57783-36-5,57783-38-7,57783-40-1,57783-42-3,58525-46-5,58525-47-6,58525-48-7,62182-01-8,62182-02-9,63864-94-8,65310-00-1,65941-62-0,68069-80-7,71116-57-9,72274-54-5,72274-55-6,73036-22-3,83198-64-5,85505-15-3,102517-74-8,109718-80-1,109718-81-2,125280-09-3,129172-95-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; water; for 96h; under 2068.65 Torr;

DOI:10.1016/j.carres.2007.11.009

upstream raw materials:

methanol

L-Fucose

6-deoxy-L-galactose

methyl-2,3-di-O-acetyl-4-O-benzoyl-6-desoxy-α-D-arabino-hex-5-enopyranoside

Downstream raw materials:

L-galacto-2,4,5-Trihydroxy-3-methoxy-hexanal

D-Fucose

1-O-methyl 2,3,4-tri-O-benzyl-L-fucopyranoside

Methyl 3-O-benzyl-α-L-rhamnopyranoside

Refernces

• 1、 Khatri, Hem Raj,Bhattarai, Bijay,Kaplan, Will,Li, Zhongzheng,Curtis Long, Marcus John,Aye, Yimon,Nagorny, Pavel. "Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation". supporting information. p. 4849 - 4860. Retrieved 2019/03/26.
• 2、 Shen, Zhengnan,Mobarak, Hani,Li, Wei,Widmalm, G?ran,Yu, Biao. "Synthesis of β-(1→2)-Linked 6-Deoxy- l -altropyranose Oligosaccharides via Gold(I)-Catalyzed Glycosylation of an ortho-Hexynylbenzoate Donor". . p. 3062 - 3071. Retrieved 2017/03/23.